Water → 3-Cyclopentyloxy-4-methoxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

To the solution of 15.22 g (100 mmoles) of isovanilline in 125 ml of dimethylsulphoxide, 27 g of powdered anhydrous potassium carbonate are added. The suspension is stirred at 60° C. for 30 minutes and then 12.9 ml (120 mmoles) of cyclopentyl bromide are added at 60° C. during 60 minutes. Then the suspension is stirred at the same temperature 8 hours, cooled to 25° C. and poured into 500 ml of water. The aqueous emulsion is extracted four times with 100 ml of ether. The collected ethereal phases are washed twice with 20 ml of 1 N sodium hydroxide solution, dried over anhydrous magnesium sulphate and evaporated. To the oily residue 100 ml of benzene are added and the evaporation is repeated. The remained oil is fractionally distilled in vacuo to give 20.65 g (94%) of title compound, b.p. 136°-138° C./0.01 Hgmm.

Provenance & Evidence