Chloroacetic Acid → 2-(Tert-butoxy)acetic acid

Participants

Reaction Steps

A suspension of sodium t-butoxide (24.1 g) in t-butanol (150 ml) was cooled in a water bath and treated drop-wise with a solution of chloroacetic acid (11.4 g) in t-butanol (30 ml). The mixture was heated under reflux for 5 h then concentrated in vacuo. The resultant white solid was dried in vacuo for 16 h then water (10 ml) was added and the mixture was filtered. The filtrate was treated with diethyl ether (150 ml), then cooled in an ice bath, stirred and acidified to pH1 with 2N sulphuric acid. The layers were separated and the aqueous layer was further extracted with diethyl ether. The combined organic extracts were dried MgSO4) and concentrated in vacuo to afford Intermediate 32 (11.1 g). 1H NMR (400 MHz, CDCl3, δ ppm) 1.27 (9H, s), 4.04 (2H, s).

Provenance & Evidence