methyl 2-(2-hydroxyphenyl)propanoate

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

Procedure: To a solution of methyl 2-hydroxyphenylacetic acid methyl ester (1000 mg, 6.02 mmol) in nitrobenzene (10 ml) was added heptanoyl chloride (900 mg, 6.02 mmol), followed by aluminium chloride (1.6 g, 12.0 mmol, 2 equiv). The solution was heated to 60 C for 18 h, then cooled on ice before quenching with aqueous hydrochloric acid (1 M, 50 ml). The mixture was extracted with dichloromethane. (3×50 ml) and concentrated. Chromatography on silica gel using ethyl acetate/petroleum spirits (20:80) as eluant gave a semi-solid yellow residue. Recrystallization from dichloromethane/petroleum spirits at −15 C gave the title compound as a pale yellow solid (129 mg). Mp 64-67° C.; The solution was heated to 60 C for 18 h cooled on ice before quenching with aqueous hydrochloric acid (1 M, 50 ml) The mixture was extracted with dichloromethane (3×50 ml) and concentrated gave a semi-solid yellow residue Recrystallization from dichloromethane/petroleum spirits at −15 C

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

Procedure: To a solution of methyl 2-hydroxyphenylacetic acid methyl ester (1000 mg, 6.02 mmol) in nitrobenzene (10 ml) was added heptanoyl chloride (900 mg, 6.02 mmol), followed by aluminium chloride (1.6 g, 12.0 mmol, 2 equiv). The solution was heated to 60 C for 18 h, then cooled on ice before quenching with aqueous hydrochloric acid (1 M, 50 ml). The mixture was extracted with dichloromethane. (3×50 ml) and concentrated. Chromatography on silica gel using ethyl acetate/petroleum spirits (20:80) as eluant gave a semi-solid yellow residue. Recrystallization from dichloromethane/petroleum spirits at −15 C gave the title compound as a pale yellow solid (129 mg). Mp 64-67° C.; The solution was heated to 60 C for 18 h cooled on ice before quenching with aqueous hydrochloric acid (1 M, 50 ml) The mixture was extracted with dichloromethane (3×50 ml) and concentrated gave a semi-solid yellow residue Recrystallization from dichloromethane/petroleum spirits at −15 C

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

Procedure: To a solution of methyl 2-hydroxyphenylacetic acid methyl ester (1000 mg, 6.02 mmol) in nitrobenzene (10 ml) was added heptanoyl chloride (900 mg, 6.02 mmol), followed by aluminium chloride (1.6 g, 12.0 mmol, 2 equiv). The solution was heated to 60 C for 18 h, then cooled on ice before quenching with aqueous hydrochloric acid (1 M, 50 ml). The mixture was extracted with dichloromethane. (3×50 ml) and concentrated. Chromatography on silica gel using ethyl acetate/petroleum spirits (20:80) as eluant gave a semi-solid yellow residue. Recrystallization from dichloromethane/petroleum spirits at −15 C gave the title compound as a pale yellow solid (129 mg). Mp 64-67° C.; The solution was heated to 60 C for 18 h cooled on ice before quenching with aqueous hydrochloric acid (1 M, 50 ml) The mixture was extracted with dichloromethane (3×50 ml) and concentrated gave a semi-solid yellow residue Recrystallization from dichloromethane/petroleum spirits at −15 C