2-phenylethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of commercially available 5-bromo-2-chlorobenzoic acid (5 g, 21.23 mmol) in 30 mL of anhydrous DCM was added a catalytic amount of DMF followed by oxalyl chloride (1.95 mL, 22.3 mmol) and stirred for 2 h at room temperature. A mixture of aluminum trichloride (3.68 g, 27.6 mmol) and phenethyl acetate (3.38 mL, 21.23 mmol) in 15 mL DCM was cooled in an ice-bath and the acid chloride was transferred to it using a canula. The mixture was stirred at room temperature for 4 h. The mixture was poured into 100 mL of ice-cold water and the organic layer was isolated. The aqueous solution was extracted with 25 mL DCM. The combined organic solution was washed with brine (25 mL) and dried (Na2SO4), filtered and evaporated. Purification on silica gel using an ISCO column with 5:1 hexane:EtOAc followed by 10:1 hexane:EtOAc gave intermediate BF (2.1 g, yield 26%). 1H NMR (300 MHz, CDCl3): δ 8.12 (d, J=2.4 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.59 (d, J=2.7 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.36 (s, 1H), 7.33 (d, J=8.4 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 4.31 (t, J=6.9, 6.6 Hz, 2H), 3.01 (t, J=6.9, 6.6 Hz, 2H), 2.04 (s, 3H). was cooled in an ice-bath The mixture was stirred at room temperature for 4 h the organic layer was isolated The aqueous solution was extracted with 25 mL DCM The combined organic solution was washed with brine (25 mL) dried (Na2SO4) filtered evaporated Purification on silica gel using an ISCO column with 5:1 hexane EtOAc gave intermediate BF (2.1 g, yield 26%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isobutyryl chloride (114 g, 1.07 mol) is added drop wise at −5 to 0° C. over 40 minutes to 295 g (2.21 mol) of anhydrous aluminum chloride in 160 ml of methylene chloride. Stirring is continued for 30 min, and 2-phenylethyl acetate (164.2 g, 1.00 mol) is then added drop wise at −5 to 0° C. over 2 hours. The mixture is stirred an additional 4 hours at −5 to 0° C., and then poured into a mixture of concentrated hydrochloric acid and ice. The organic layer is washed with water, dried and concentrated to give 190.5 g of crude 2-(4-isobutyrylphenyl)ethyl acetate, a colorless liquid. The mixture is stirred an additional 4 hours at −5 to 0° C. The organic layer is washed with water dried concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aluminum chloride (48.2 g) was added to dichloroethane (400 ml) in a stream of nitrogen and the mixture was stirred at room temperature. Then, phenethyl acetate (39.6 g) and undecanoyl chloride (52.7 g) were dropwise added thereto under ice-cooling and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20) to give the subject compound (34.5 g) as pale yellow crystals. under ice-cooling the mixture was stirred at room temperature overnight extracted with diethyl ether The ether layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was distilled away the residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aluminum chloride (111.8 g) was added to dichloroethane (500 ml) in a stream of nitrogen and the mixture was stirred at room temperature. Then, phenethyl acetate (91.8 g) and decanoyl chloride (100 g) were dropwise added thereto under ice-cooling and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20) to give 61.3 g of the subject compound (yield 38%) as an oily substance. under ice-cooling the mixture was stirred at room temperature overnight extracted with diethyl ether The ether layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was distilled away the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aluminum chloride (48.2 g) was added to dichloroethane (400 ml) in a stream of nitrogen and the mixture was stirred at room temperature. Then, phenethyl acetate (39.6 g) and undecanoyl chloride (52.7 g) were dropwise added thereto under ice-cooling and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20) to give the subject compound (34.5 g) as pale yellow crystals. under ice-cooling the mixture was stirred at room temperature overnight extracted with diethyl ether The ether layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was distilled away the residue obtained was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aluminum chloride (111.8 g) was added to dichloroethane (500 ml) in a stream of nitrogen and the mixture was stirred at room temperature. Then, phenethyl acetate (91.8 g) and decanoyl chloride (100 g) were dropwise added thereto under ice-cooling and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20) to give 61.3 g of the subject compound (yield 38%) as an oily substance. under ice-cooling the mixture was stirred at room temperature overnight extracted with diethyl ether The ether layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was distilled away the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Aluminum chloride (111.8 g) was added to dichloroethane (500 ml) in a stream of nitrogen and the mixture was stirred at room temperature. Then, phenethyl acetate (91.8 g) and decanoyl chloride (100 g) were dropwise added thereto under ice-cooling and the mixture was stirred at room temperature overnight. The reaction mixture was poured into ice water and extracted with diethyl ether. The ether layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20) to give 61.3 g of the subject compound (yield 38%) as an oily substance. under ice-cooling the mixture was stirred at room temperature overnight extracted with diethyl ether The ether layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was distilled away the residue was purified by silica gel column chromatography (eluent; ethyl acetate:hexane=1:20)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of commercially available 5-bromo-2-chlorobenzoic acid (5 g, 21.23 mmol) in 30 mL of anhydrous DCM was added a catalytic amount of DMF followed by oxalyl chloride (1.95 mL, 22.3 mmol) and stirred for 2 h at room temperature. A mixture of aluminum trichloride (3.68 g, 27.6 mmol) and phenethyl acetate (3.38 mL, 21.23 mmol) in 15 mL DCM was cooled in an ice-bath and the acid chloride was transferred to it using a canula. The mixture was stirred at room temperature for 4 h. The mixture was poured into 100 mL of ice-cold water and the organic layer was isolated. The aqueous solution was extracted with 25 mL DCM. The combined organic solution was washed with brine (25 mL) and dried (Na2SO4), filtered and evaporated. Purification on silica gel using an ISCO column with 5:1 hexane:EtOAc followed by 10:1 hexane:EtOAc gave intermediate BF (2.1 g, yield 26%). 1H NMR (300 MHz, CDCl3): δ 8.12 (d, J=2.4 Hz, 1H), 7.71 (d, J=8.4 Hz, 1H), 7.59 (d, J=2.7 Hz, 1H), 7.56 (d, J=8.4 Hz, 1H), 7.36 (s, 1H), 7.33 (d, J=8.4 Hz, 1H), 7.30 (d, J=8.4 Hz, 1H), 4.31 (t, J=6.9, 6.6 Hz, 2H), 3.01 (t, J=6.9, 6.6 Hz, 2H), 2.04 (s, 3H). was cooled in an ice-bath The mixture was stirred at room temperature for 4 h the organic layer was isolated The aqueous solution was extracted with 25 mL DCM The combined organic solution was washed with brine (25 mL) dried (Na2SO4) filtered evaporated Purification on silica gel using an ISCO column with 5:1 hexane EtOAc gave intermediate BF (2.1 g, yield 26%)

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isobutyryl chloride (114 g, 1.07 mol) is added drop wise at −5 to 0° C. over 40 minutes to 295 g (2.21 mol) of anhydrous aluminum chloride in 160 ml of methylene chloride. Stirring is continued for 30 min, and 2-phenylethyl acetate (164.2 g, 1.00 mol) is then added drop wise at −5 to 0° C. over 2 hours. The mixture is stirred an additional 4 hours at −5 to 0° C., and then poured into a mixture of concentrated hydrochloric acid and ice. The organic layer is washed with water, dried and concentrated to give 190.5 g of crude 2-(4-isobutyrylphenyl)ethyl acetate, a colorless liquid. The mixture is stirred an additional 4 hours at −5 to 0° C. The organic layer is washed with water dried concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Isobutyryl chloride (114 g, 1.07 mol) is added drop wise at −5 to 0° C. over 40 minutes to 295 g (2.21 mol) of anhydrous aluminum chloride in 160 ml of methylene chloride. Stirring is continued for 30 min, and 2-phenylethyl acetate (164.2 g, 1.00 mol) is then added drop wise at −5 to 0° C. over 2 hours. The mixture is stirred an additional 4 hours at −5 to 0° C., and then poured into a mixture of concentrated hydrochloric acid and ice. The organic layer is washed with water, dried and concentrated to give 190.5 g of crude 2-(4-isobutyrylphenyl)ethyl acetate, a colorless liquid. The mixture is stirred an additional 4 hours at −5 to 0° C. The organic layer is washed with water dried concentrated

Conditions: temp:0.00; pressure:0.00; stir: