Methylparaben → HCID 69638743, compound

Participants

Reaction Steps

A solution of 14.36 g (82.5 mmol) of diethyl-azo-dicarboxylate in 50 ml of tetrahydrofuran was added within 30 minutes to a solution of 11.4 g (75.0 mmol) 4-hydroxy-benzoic acid methyl ester, 20.65 g (78.8 mmol) of triphenylphosphin and 13.5 g (75.0 mmol) of 4-benzyloxy-1-butanol dissolved in 100 ml of tetrahydrofuran. The reaction mixture was then stirred for 1 hour at room temperature, 1 g of triphenylphosphin was added and stirring continued for 1 hour at room temperature and for 30 minutes at reflux. The reaction mixture was then diluted with 200 ml of hexane and filtered. The filtrate was poured into 200 ml of a saturated potassium carbonate solution and extracted 3 times with 200 ml of ethylacetate. The combined ethylacetate phases were washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 98:2 v/v mixture of dichloromethane and ether as the eluent giving 21.8 g (92.4%) 4-(4-benzyloxy-butoxy)-benzoic acid methyl ester as colorless viscous oil, MS: 314 (M+).

Provenance & Evidence