tridecane

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: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:; See reaction.notes.procedure_details.

実験手順: 1.32 mL (10.0 mmol) 2-tetralone in 5 mL of THF was added to a solution of 5.77 mL (12.0 mmol) 2.08 M phenylmagnesium chloride in THF at 0° C. The mixture was allowed to warm to room temperature, and was then stirred for an additional 1 hour. Tridecane (1.22 mL; 5.00 mmol; internal GC standard) was added, the mixture was cooled to 0°, 10 mL of 6N HCl was added. The mixture was heated to 65° and vigorously stirred for 4 hours. The mixture was then cooled to room temperature and diluted with toluene. GC analysis of the organic phase showed the presence of 2.9 mmol 2-phenyl-3,4-dihydronaphthalene (29% yield on 2-tetralone) and 4.6 mmol 2-tetralone (46% recovery). No benzylic alcohol intermediate from addition of the arylmagnesium reagent to the ketone was detected, indicating that its dehydration to the vinylaromatic had been completed by the warm acid treatment. the mixture was cooled to 0° The mixture was heated to 65° vigorously stirred for 4 hours The mixture was then cooled to room temperature

反応条件: temp:190.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4,5-difluorophthalic acid (0.55 grams, 2.7 mmole) was added to a slurry of cupric oxide (10% by weight of starting material) in 5 ml. of N-methyl-2-pyrrolidone solvent. n-tridecane (0.25 grams) was added as an internal standard. The mixture was heated to 190° C. for 3 hours, at which time GC analysis indicated complete consumption of the starting material and conversion to 3,4-difluorobenzoic acid in an 87% yield, based upon the internal standard, corrected for response factors. consumption of the starting material and conversion to 3,4-difluorobenzoic acid in an 87% yield

反応条件: temp:190.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 4,5-difluorophthalic anhydride (0.5 grams, 2.7 mmole) was added to a slurry of cupric oxide (5% by weight of starting material) in 5 ml. of N-methyl-2-pyrrolidone. n-tridecane (0.25 grams) was added as an internal standard. The mixture was heated to 190° C. for 3 hours, at which time GC analysis indicated complete consumption of the starting material and conversion to 3,4-difluorobenzoic acid in an 85% yield, based upon the internal standard, corrected for response factors. consumption of the starting material and conversion to 3,4-difluorobenzoic acid in an 85% yield

反応条件: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: A slurry of magnesium bromide (0.74 g; 4.0 mmol) in THF (3 mL) was treated at room temperature with phenyllithium (2.4 mL of 1.7M solution; 4.0 mmol). The solution was heated at 60° C. for 30 min, and was then treated at 600 with lithium t-butoxide (4.4 mL of 1.0M solution in THF; 4.4 mmol) and heating was continued for lh. The reaction solution was cooled to room temperature and treated with a solution of 4-methoxybenzonitrile (0.27 g, 2.0 mmol), dichlorobis(trimethylphosphine)nickel (0.028 g; 5 mol %), and tridecane (0.18 g; 1.0 mmol; internal GC standard) in THF (2 mL). The reaction was then heated to 60° and stirred for 2 h. A sample was withdrawn and quenched in a mixture of 1M sodium citrate (aq) and ether. GC analysis of the organic phase of the hydrolyzed reaction sample showed the presence of 1.67 mmol (84% yield) of 4-phenylanisole, 0.18 mmol of 4-methoxybenzophenone imine, and no remaining 4-methoxybenzonitrile in the reaction mixture. heating The reaction solution was cooled to room temperature The reaction was then heated to 60° A sample was withdrawn quenched in a mixture of 1M sodium citrate (aq) and ether