Dichloromethane → (3-Methoxyphenoxy)acetyl chloride

Participants

Reaction Steps

A 500 mL flask fitted with a stir-bar, addition funnel, and an Ar inlet was charged with 3-methoxyphenoxyacetic acid (20.0 g, 110 mmol), CH2Cl2 (120 mL), and DMF (0.2 mL). Oxalyl chloride (2M in CH2Cl2, 69 mL, 137 mmol) was added to the resultant solution over 45 min forming an orange solution. The mixture stirred overnight at rt. The solution was concentrated in vacuo to give 22.7 g of 47b as an orange oil (100%). HPLC analysis (15:10:75 H2O:A1:MeOH) showed a purity of 93% with a retention time of 3.9 min.

Provenance & Evidence