Reaction #1328425

Reaction equation

hydrochloric acid

allyl bromide

potassium hydroxide

methyl 2-hydroxy-3-formyl-4-methoxybenzoate

→

methyl 2-allyloxy-3-formyl-4-methoxybenzoate

Yield 36.0%

Solvents

dimethyl sulfoxide

Conditions

Workup

1. 1
   Extractionextracted with ethyl acetate
2. 2
   WashThe combined organic phases were washed with water
3. 3
   Otherdried
4. 4
   Otherthe solvent was removed

Procedure

At room temperature, 23.2 g (0.192 mol) of allyl bromide were added dropwise to a mixture of 21.0 g (0.375 mol) of potassium hydroxide and 20.2 g (0.096 mol) of methyl 2-hydroxy-3-formyl-4-methoxybenzoate in 500 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 4 hours. The mixture was subsequently stirred into 1.5 l of 3% strength aqueous hydrochloric acid and extracted with ethyl acetate. The combined organic phases were washed with water and dried, and the solvent was removed. Silica gel chromatography using cyclohexane/ethyl acetate=1:2 gave 7.7 g (36%) of methyl 2-allyloxy-3-formyl-4-methoxybenzoate in the form of a yellowish oil.

Source