Reaction #47080

Reaction equation

benzyl alcohol

ethyl diazoacetate

→

product 390

Yield 93.2%

Benzyloxyacetic acid ethyl ester

Yield 93.2%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.DISTILLATIONdistilled at 110° C.

Procedure

To a solution of benzyl alcohol (1.04 mL, 10.0 mmol) in dichloromethane (30 mL) is added rhodium (II) acetate dimer (40 mg) followed by ethyl diazoacetate (1.14 g, 10.0 mmol). The reaction mixture is stirred at RT for 20 min. The reaction mixture is rotary evaporated, and the residue is vacuum distilled at 110° C. to give 1.81 g of the product 390. 1H NMR (CDCl3) δ 7.4-7.26 (m, 5H), 4.65 (s, 2H), 4.23 (q, 2H), 4.10 (s, 2H), 1.30 (t, 3H).

Source