Reaction #47083

Reaction equation

3-methylbenzyl alcohol

ethyl diazoacetate

→

product 396

Yield 101.9%

(3-Methylbenzyloxy)acetic acid ethyl ester

Yield 101.9%

Solvents

heptane

dichloromethane

Conditions

Workup

1. 1
   Filtrationfiltered through Celite
2. 2
   Otherthe filtrate is evaporated
3. 3
   workup.DISTILLATIONdistilled at 150° C.

Procedure

To a solution of 3-methylbenzyl alcohol (1.08 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at RT for 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 1.91 g of the product 396. 1H NMR (CDCl3) δ 7.3-7.1 (m, 4H), 4.60 (s, 2H), 4.23 (q, 2H), 4.09 (s, 2H), 2.36 (s, 3H), 1.29 (t, 311); MS: m/z 209 (M++1).

Source