Reaction #47098

Reaction equation

2-phenoxyethan-1-ol

ethyl diazoacetate

→

product 440

Yield 82.8%

(2-Phenoxy)ethoxyacetic acid ethyl ester

Yield 82.8%

Solvents

heptane

dichloromethane

Conditions

Workup

1. 1
   Filtrationfiltered
2. 2
   OtherThe filtrate is evaporated
3. 3
   workup.DISTILLATIONthe residue vacuum distilled

Procedure

To a solution of 2-phenoxyethan-1-ol (1.5 mL, 12.7 mmol) in dichloromethane (50 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (1.1 mL, 10.5 mmol). The reaction mixture is stirred at rt overnight. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue vacuum distilled to give 1.95 g of the product 440. 1H NMR (CDCl3) δ 7.40-7.25 (m, 2 H), 7.10-6.90 (m, 3 H), 4.30-4.15 (m, 5 H), 4.15-4.05 (m, 1 H), 4.05-3.90 (s, 2 H), 1.28 (t, 3 H)

Source