Chloroacetic Acid → [3-(Propan-2-yl)phenoxy]acetyl chloride

Participants

Reaction Steps

A mixture of 3-isopropylphenoxyacetic acid (prepared by the reaction of 3-isopropylphenol with chloroacetic acid in the presence of sodium hydroxide, 5.0 g, 25.8 mmol) and SOCl2 (5.0 mL, 8.2 g, 68.8 mmol) in 10 mL of benzene was refluxed for 2 h. Thereafter volatile materials were removed by vacuum distillation to give 3-isopropylphenoxyacetic acid chloride as a light brown oil. To an ice-bath cooled solution of 4-aminobutyric acid (5.3 g, 51.6 mmol, 2.0 eq) and NaOH (2.0 g, 51.6 mmol) in 60 mL of H2O and 80 mL of CH3CN were added drop-wise the acid chloride in 40 mL of CH3CN and NaHCO3 (3.3 g, 38.7 mmol, 1.5 eq) in 50 mL of H2O. The resulting mixture was stirred vigorously for 5 h.

Provenance & Evidence