Acetate → Phenoxyacetic Acid

Participants

Reaction Steps

A portion of 16a (15.8 g; 29.9 mmol) was dissolved in 748 mL of MeOH. 35% aq. KOH (262 mL) was added in portions over 5 min. The reaction was heated to reflux. After 1 h TLC (30% ethyl acetate:hexane) indicated no starting material remained. After 4 h, TLC (100% ethyl acetate) indicated a heavy UV active spot above the origin. The reaction mixture was cooled to RT, then placed in an ice bath. 2M HCl (600 mL) was added to acidify the reaction to pH 5. The reaction mixture was diluted with 1.6 L of ethyl acetate and washed with sat. NaCl (1.6 L). The organic layer was dried over anhydrous sodium sulfate. The solvent was filtered through a sintered glass funnel. The filtrate was concentrated in vacua to recover 15.1 g of 17 as viscous oil which was taken onto the next step.

Provenance & Evidence