2-ethyl-2-(hydroxymethyl)hexanoic acid

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 113 ml (0.305 mol) of n-butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 46 ml of dissopropylamine (0.327 mol) in 320 ml of THF and the mixture is stirred at 0° C. for 30 min (Solution 1). 40 g (0.277 mol) of 2-ethylhexanoic acid are added dropwise at 25° C. to a suspension of 7 g of NaH 95% (0.277 mol) in 320 ml of THF within approx. 15 min, and the reaction mixture is stirred at 50° C. for 30 min (Solution 2). Solution 1 is added at 0° C. to Solution 2 and subsequently heated to 50° C. for 1.5 h. The clear solution is cooled to −20° C. and admixed with 25 g (0.833 mol) of paraformaldehyde. After 10 min, the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N HCl. The organic phase is removed, the aqueous phase is re-extracted once with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 70% (GC). The clear solution is cooled to −20° C. The organic phase is removed the aqueous phase is re-extracted once with MTBE the combined organic phases are concentrated on a rotary evaporator

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 113 ml (0.305 mol) of n-butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 46 ml of disiopropylamine (0.327 mol) in 320 ml of THF and the mixture is stirred at 0° C. for 30 min (Solution 1). 40 g (0.277 mol) of 2-ethylhexanoic acid are added dropwise at 25° to a suspension of 7 g of NaH 95% (0.277 mol) in 320 ml of THF within approx. 15 min, and the reaction mixture is stirred at 50° C. for 30 min (Solution 2). Solution 1 is added at 0° C. to Solution 2 and subsequently heated to 50° C. for 1.5 h. The clear solution is cooled to 0° C. and admixed with 25 g (0.833 mol) of paraformaldehyde. After 10 min, the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N HCl. The organic phase is removed, the aqueous phase is re-extracted 1× with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 71% (GC). The clear solution is cooled to 0° C. The organic phase is removed the aqueous phase is re-extracted 1× with MTBE the combined organic phases are concentrated on a rotary evaporator

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 113 ml (0.305 mol) of n-butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 46 ml of disiopropylamine (0.327 mol) in 320 ml of THF and the mixture is stirred at 0° C. for 30 min (Solution 1). 40 g (0.277 mol) of 2-ethylhexanoic acid are added dropwise at 25° to a suspension of 7 g of NaH 95% (0.277 mol) in 320 ml of THF within approx. 15 min, and the reaction mixture is stirred at 50° C. for 30 min (Solution 2). Solution 1 is added at 0° C. to Solution 2 and subsequently heated to 50° C. for 1.5 h. The clear solution is cooled to 0° C. and admixed with 25 g (0.833 mol) of paraformaldehyde. After 10 min, the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N HCl. The organic phase is removed, the aqueous phase is re-extracted 1× with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 71% (GC). The clear solution is cooled to 0° C. The organic phase is removed the aqueous phase is re-extracted 1× with MTBE the combined organic phases are concentrated on a rotary evaporator

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 27 ml (72.9 mmol) of n butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 10.9 ml of diisopropylamine (77.5 mmol) in 60 ml of THF, and the mixture is stirred at 0° C. for 30 min. Within 10 min, 5 g (34.7 mmol) of 2-ethylhexanoic acid are added dropwise at 0° C. and the reaction mixture is heated to 50° C. for 1.5 h. The clear solution is cooled to 0° C. and admixed with 3.1 g (103 mmol) of paraformaldehyde. After 10 min at 0° C., the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N of HCl. The organic phase is removed, the aqueous phase is re-extracted once with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 89% (GC). Within 10 min the reaction mixture is heated to 50° C. for 1.5 h The clear solution is cooled to 0° C. After 10 min at 0° C. the mixture is stirred at RT for 18 h The organic phase is removed the aqueous phase is re-extracted once with MTBE the combined organic phases are concentrated on a rotary evaporator

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 27 ml (72.9 mmol) of n-butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 10.9 ml of diisopropylamine (77.5 mmol) in 60 ml of THF, and the mixture is stirred at 0° C. for 30 min. Within 10 min, 5 g (34.7 mmol) of 2-ethylhexanoic acid are added dropwise at 0° C. and the reaction mixture is heated at 50° C. for 1.5 h. The clear solution is cooled to −20° C. and admixed with 3.1 g (103 mmol) of paraformaldehyde. After 10 min at −20° C., the mixture is stirred at RT for 2 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N HCl. The organic phase is removed, the aqueous phase is re-extracted once with MTBE and the combined organic phases are concentrated on a rotary evaporator. The crude product (85% yield (GC)) can be purified further by distillation (b.p.: 121° C., 0.2 mbar). Alternatively, it is also possible to crystallize the sodium salt of the product from aqueous solution in pure form. The pure product of the free 2-ethyl-2-hydroxymethylhexanoic acid, which is typically obtained as a viscous oil, crystallizes slowly at RT (melting point: 45-46° C.). Alternatively, the product can also be crystallized from a suitable solvent, for example pentane, hexane, heptane or petroleum ether. Within 10 min the reaction mixture is heated at 50° C. for 1.5 h The clear solution is cooled to −20° C. After 10 min at −20° C. the mixture is stirred at RT for 2 h The organic phase is removed the aqueous phase is re-extracted once with MTBE the combined organic phases are concentrated on a rotary evaporator The crude product (85% yield (GC)) can be purified further by distillation (b.p.: 121° C., 0.2 mbar) to crystallize the sodium salt of the product from aqueous solution in pure form

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 113 ml (0.305 mol) of n-butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 46 ml of dissopropylamine (0.327 mol) in 320 ml of THF and the mixture is stirred at 0° C. for 30 min (Solution 1). 40 g (0.277 mol) of 2-ethylhexanoic acid are added dropwise at 25° C. to a suspension of 7 g of NaH 95% (0.277 mol) in 320 ml of THF within approx. 15 min, and the reaction mixture is stirred at 50° C. for 30 min (Solution 2). Solution 1 is added at 0° C. to Solution 2 and subsequently heated to 50° C. for 1.5 h. The clear solution is cooled to −20° C. and admixed with 25 g (0.833 mol) of paraformaldehyde. After 10 min, the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N HCl. The organic phase is removed, the aqueous phase is re-extracted once with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 70% (GC). The clear solution is cooled to −20° C. The organic phase is removed the aqueous phase is re-extracted once with MTBE the combined organic phases are concentrated on a rotary evaporator

反応条件: temp:50.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 113 ml (0.305 mol) of n-butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 46 ml of disiopropylamine (0.327 mol) in 320 ml of THF and the mixture is stirred at 0° C. for 30 min (Solution 1). 40 g (0.277 mol) of 2-ethylhexanoic acid are added dropwise at 25° to a suspension of 7 g of NaH 95% (0.277 mol) in 320 ml of THF within approx. 15 min, and the reaction mixture is stirred at 50° C. for 30 min (Solution 2). Solution 1 is added at 0° C. to Solution 2 and subsequently heated to 50° C. for 1.5 h. The clear solution is cooled to 0° C. and admixed with 25 g (0.833 mol) of paraformaldehyde. After 10 min, the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N HCl. The organic phase is removed, the aqueous phase is re-extracted 1× with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 71% (GC). The clear solution is cooled to 0° C. The organic phase is removed the aqueous phase is re-extracted 1× with MTBE the combined organic phases are concentrated on a rotary evaporator

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 27 ml (72.9 mmol) of n butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 10.9 ml of diisopropylamine (77.5 mmol) in 60 ml of THF, and the mixture is stirred at 0° C. for 30 min. Within 10 min, 5 g (34.7 mmol) of 2-ethylhexanoic acid are added dropwise at 0° C. and the reaction mixture is heated to 50° C. for 1.5 h. The clear solution is cooled to 0° C. and admixed with 3.1 g (103 mmol) of paraformaldehyde. After 10 min at 0° C., the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N of HCl. The organic phase is removed, the aqueous phase is re-extracted once with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 89% (GC). Within 10 min the reaction mixture is heated to 50° C. for 1.5 h The clear solution is cooled to 0° C. After 10 min at 0° C. the mixture is stirred at RT for 18 h The organic phase is removed the aqueous phase is re-extracted once with MTBE the combined organic phases are concentrated on a rotary evaporator

反応条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 27 ml (72.9 mmol) of n-butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 10.9 ml of diisopropylamine (77.5 mmol) in 60 ml of THF, and the mixture is stirred at 0° C. for 30 min. Within 10 min, 5 g (34.7 mmol) of 2-ethylhexanoic acid are added dropwise at 0° C. and the reaction mixture is heated at 50° C. for 1.5 h. The clear solution is cooled to −20° C. and admixed with 3.1 g (103 mmol) of paraformaldehyde. After 10 min at −20° C., the mixture is stirred at RT for 2 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N HCl. The organic phase is removed, the aqueous phase is re-extracted once with MTBE and the combined organic phases are concentrated on a rotary evaporator. The crude product (85% yield (GC)) can be purified further by distillation (b.p.: 121° C., 0.2 mbar). Alternatively, it is also possible to crystallize the sodium salt of the product from aqueous solution in pure form. The pure product of the free 2-ethyl-2-hydroxymethylhexanoic acid, which is typically obtained as a viscous oil, crystallizes slowly at RT (melting point: 45-46° C.). Alternatively, the product can also be crystallized from a suitable solvent, for example pentane, hexane, heptane or petroleum ether. Within 10 min the reaction mixture is heated at 50° C. for 1.5 h The clear solution is cooled to −20° C. After 10 min at −20° C. the mixture is stirred at RT for 2 h The organic phase is removed the aqueous phase is re-extracted once with MTBE the combined organic phases are concentrated on a rotary evaporator The crude product (85% yield (GC)) can be purified further by distillation (b.p.: 121° C., 0.2 mbar) to crystallize the sodium salt of the product from aqueous solution in pure form