Reaction #75438

Reaction equation

5-methyl-4-hexenoic acid

diazomethane

→

title product

Methyl 5-methyl-4-hexenoate

Solvents

ether

ether

Conditions

Workup

1. 1
   OtherThe solvent was then evaporated under vacuum

Procedure

Freshly prepared diazomethane in ether was added to an ice-cooled solution of 5-methyl-4-hexenoic acid (4.5 g, 35.16 mmol) in ether (10 mL) until the solution became slightly yellow in color. The solvent was then evaporated under vacuum to afford the title product as a colorless liquid in near quantitative yield (4.90 g). This product was used in the next reaction step without further purification. 1H NMR (CDCl3) δ1.62 & 1.68[2s, 6H, C(CH3)2], 2.30[m, 4H, (CH2)2], 3.69(s, 3H, COOCH3) and 5.07(t, 1H, CH).

Source