Reaction #6024

Reaction equation

methyl 4-hydroxy-3-propenylbenzoate

potassium carbonate

allyl bromide

→

title compound

Yield 87.0%

methyl 3-(2-propen-1-yl)-4-(2-propen-1-yloxy)benzoate

Yield 87.0%

Solvents

acetone

Conditions

Workup

1. 1
   FiltrationThe mixture was filtered through Celite
2. 2
   Washthe filter cake was washed with more acetone and dichloromethane
3. 3
   OtherAfter removing the solvents
4. 4
   workup.DISTILLATIONthe resulting oil was distilled under high vacuum

Procedure

A solution of 3.04 g (15.8 mmol) of methyl 4-hydroxy-3-propenylbenzoate (Example 42, Step B) was refluxed with anhydrous potassium carbonate (4.37 g, 2 equiv) and allyl bromide (3.5 mL, 2.5 equiv) in acetone overnight. The mixture was filtered through Celite and the filter cake was washed with more acetone and dichloromethane. After removing the solvents, the resulting oil was distilled under high vacuum to give 3.2 g (87%) of the title compound.

Source