Reaktion #47083

Reaktionsgleichung

3-methylbenzyl alcohol

ethyl diazoacetate

→

product 396

Ausbeute 101.9%

(3-Methylbenzyloxy)acetic acid ethyl ester

Ausbeute 101.9%

Lösungsmittel

heptane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle