Reaction #54889

Reaction equation

diazomethane

4-(4-acetyl-8-hydroxytridecyl)benzoic acid

Acetic acid

→

methyl 4-(4-acetyl-8-hydroxytridecyl)benzoate

Solvents

ether

ether

Conditions

Workup

1. 1
   Otherto destroy the excess diazomethane
2. 2
   Washthe solution is washed with dilute sodium bicarbonate solution and water
3. 3
   Dryingdried over sodium sulfate
4. 4
   OtherEvaporation of volatile materials at reduced pressure

Procedure

A solution of diazomethane (approximately 2.5 g., 0.06 mole) in ether (100 ml.) is mixed with a solution of 4-(4-acetyl-8-hydroxytridecyl)benzoic acid (10.8 g., 0.03 mole) in ether (50 ml.). The resulting solution is allowed to stand 4 hours at room temperature. Acetic acid is then added to destroy the excess diazomethane and the solution is washed with dilute sodium bicarbonate solution and water and dried over sodium sulfate. Evaporation of volatile materials at reduced pressure yields methyl 4-(4-acetyl-8-hydroxytridecyl)benzoate, a colorless viscous oil.

Source