Reaction #53260

Reaction equation

3-hydroxymyristic acid

triethylamine

benzyl bromide

→

benzyl 3-hydroxymyristate

Solvents

DMF

Conditions

Workup

1. 1
   OtherAfter the solvent was removed in vacuo, to the residue
2. 2
   workup.ADDITIONwere added ethyl acetate and water
3. 3
   WashThe separated ethyl acetate layer was washed twice with water
4. 4
   Dryingdried over anhydrous sodium sulfate
5. 5
   OtherAfter the ethyl acetate was removed in vacuo, purification

Procedure

To a solution of 3-hydroxymyristic acid (5.00 g) and triethylamine (2.85 g) in DMF (50 ml) was added benzyl bromide (2.43 ml) and the mixture was stirred at room temperature overnight. After the solvent was removed in vacuo, to the residue were added ethyl acetate and water. The separated ethyl acetate layer was washed twice with water and then dried over anhydrous sodium sulfate. After the ethyl acetate was removed in vacuo, purification was carried out by a silica gel column chromatography (silica gel 30 g, chloroform:methanol=100:0-10) to afford 3.69 g of benzyl 3-hydroxymyristate.

Source