methyl 2-chloropropanoate

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:110.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a one liter round bottom flask equipped with a mechanical stirrer and a thermometer was added 157.13 grams (1.14 moles--1.3 equiv.) of potassium carbonate, followed by 215.27 grams (0.875 mole--1.0 equiv.) of 89.9% pure 2-(morpholin-4-ylmethyl)-5-ethylphenol, and 230 mL (%Wt/Vol. Phenol to Solvent--93.6%) of N,N-dimethylformamide. The mixture was vigorously stirred and heated to 110° C., and then 139.3 grams (1.14 moles--1.3 equiv.) of methyl 2-chloropropanoate was added during a one hour period. Upon completion of addition, the reaction mixture was analyzed by GC, which indicated the reaction was incomplete. The reaction mixture was heated at 110° C. for seven hours. After this time, the reaction mixture was again analyzed by GC, which indicated the reaction was complete. The reaction mixture was filtered, and the orange filtrate was kept under a nitrogen atmosphere for about 48 hours. After this time, the filtrate was concentrated under vacuum at 90° C. and 10 mm of mercury to yield a red, brown liquid. The liquid was taken up in 200 mL of toluene, and the resulting solution was washed with two 500 mL portions of an aqueous saturated sodium chloride solution. The organic layer was separated from the aqueous layer, dried with magnesium sulfate, and filtered. The filtrate was concentrated under vacuum at 90° C. and 10 mm of mercury, yielding 252.7 grams of 83.6% pure methyl 2-[2-(morpholin-4-ylmethyl)-5-ethylphenoxy]propanoate (78.6% yield). The NMR spectrum was consistent with the proposed structure. To a one liter round bottom flask equipped with a mechanical stirrer Upon completion of addition The reaction mixture was heated at 110° C. for seven hours The reaction mixture was filtered After this time, the filtrate was concentrated under vacuum at 90° C. 10 mm of mercury to yield a red, brown liquid the resulting solution was washed with two 500 mL portions of an aqueous saturated sodium chloride solution The organic layer was separated from the aqueous layer dried with magnesium sulfate filtered The filtrate was concentrated under vacuum at 90° C.

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:0.00; pressure:0.00; stir:

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of m-fluorophenol (24.2 g, 0.22 mol) in 79.2 ml of 25% aqueous sodium hydroxide heated to 45° C. with an oil bath was added 29.5 ml (0.26 mol) methyl 2-chloropropionate. The reaction mixture was heated to 80° C. for 17 hours and then allowed to cool. When the temperature reached about 40° C., concentrated HCl (25 ml) was added and the reaction mixture was allowed to cool to room temperature. The reaction mixture was extracted twice with 100 ml ethyl ether. The organic layers were combined and washed with 200 ml of 1.5M aqueous sodium carbonate. The aqueous layer was separated and acidified to pH 1, by pH test paper, by adding concentrated HCl. The acidified aqueous layer was extracted with 200 ml ethyl ether. The organic layer was separated, dried with MgSO4 and filtered. The solvent was removed in vacuo to yield 17 g (41% yield) of 2-(3' -fluorophenoxy)propionic acid as a yellow solid (m.p. 72.5°-74° C.). to cool reached about 40° C. to cool to room temperature The reaction mixture was extracted twice with 100 ml ethyl ether washed with 200 ml of 1.5M aqueous sodium carbonate The aqueous layer was separated by adding concentrated HCl The acidified aqueous layer was extracted with 200 ml ethyl ether The organic layer was separated dried with MgSO4 filtered The solvent was removed in vacuo

反応条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of m-fluorophenol (24.2 g, 0.22 mol) in 79.2 ml of 25% aqueous sodium hydroxide heated to 45° C. with an oil bath was added 29.5 ml (0.26 mol) methyl 2-chloropropionate. The reaction mixture was heated to 80° C. for 17 hours and then allowed to cool. When the temperature reached about 40° C., concentrated HCl (25 ml) was added and the reaction mixture was allowed to cool to room temperature. The reaction mixture was extracted twice with 100 ml ethyl ether. The organic layers were combined and washed with 200 ml of 1.5M aqueous sodium carbonate. The aqueous layer was separated and acidified to pH 1, by pH test paper, by adding concentrated HCl. The acidified aqueous layer was extracted with 200 ml ethyl ether. The organic layer was separated, dried with MgSO4 and filtered. The solvent was removed in vacuo to yield 17 g (41% yield) of 2-(3' -fluorophenoxy)propionic acid as a yellow solid (m.p. 72.5°-74° C.). to cool reached about 40° C. to cool to room temperature The reaction mixture was extracted twice with 100 ml ethyl ether washed with 200 ml of 1.5M aqueous sodium carbonate The aqueous layer was separated by adding concentrated HCl The acidified aqueous layer was extracted with 200 ml ethyl ether The organic layer was separated dried with MgSO4 filtered The solvent was removed in vacuo