Acetic Anhydride → (4-Acetoxymethyl-phenoxy)-acetic Acid Methyl Ester

Participants

Reaction Steps

A solution of (4-hydroxymethyl-phenoxy)-acetic acid methyl ester 69 (100 grams, 509 mmol), acetic anhydride (250 mL) and pyridine (20 mL) was refluxed for 4 hours. Reaction mixture was poured in to ice water (1000 mL) and crude 70 was extracted into chloroform, dried over Na2SO4, and distilled. The crude was vacuum distilled to give pure 70 (75 grams, 61.7%) as a light yellow syrup, Bp15 206-210° C. The structure was confirmed with NMR. IHNMR (CDCl3) δ 2.05 (s, 3H,O═C—CH3), 3.78(s, 3H,ester), 4.62(s, 2H,OCH2), 5.02 (s, 2H, CH2), 6.88 (d,2H,Ar), 7.33 (d, 2H,Ar).

Provenance & Evidence