Ethanol → Ethyl (3-phenoxyphenyl)acetate

Participants

Reaction Conditions

Reaction Steps

(3-Phenoxyphenyl)acetic acid (11.5 g) and 36N aqueous sulphuric acid solution (3 cc) in ethanol (200 cc) are brought to boiling for 72 hours. After being cooled to approximately 20° C., the reaction mixture is concentrated to dryness at 50° C. under reduced pressure (20 mm Hg; 2.7 kPa). The oil is dissolved in dichloromethane (300 cc); the organic phase is washed with water (150 cc), dried over anhydrous magnesium sulphate, filtered and concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is dissolved in a mixture (20 cc) of cyclohexane and ethyl acetate (50:50 by volume), and the solution is poured onto silica (400 g) contained in a column 5 cm in diameter. Elution is performed with a mixture of cyclohexane and ethyl acetate (50:50 by volume), and the corresponding eluate is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). Ethyl (3-phenoxyphenyl)acetate (7.4 g) is thereby obtained, and is used in the crude state in the subsequent syntheses.

Provenance & Evidence