Hydrochloric Acid → HCID 15816724, compound

Participants

Reaction Conditions

Reaction Steps

4.4 g of 60% sodium hydride in mineral oil (0.11 mole) were stirred in 35 ml absolute dimethylformamide under a nitrogen atmosphere. 15.7 g (0.1 mole) 1,4-dioxaspiro[4.5]decan-8-ol were dissolved in 65 ml dimethylformamide. This solution was added drop-wise to the sodium hydride suspension. 16 ml 1-chloromethyl-3-methoxybenzene (0.11 mole), dissolved in 25 ml dimethylformamide, were then added. The mixture was stirred for 30 minutes at 60° C., poured on to ice, extracted with ether and dried over sodium sulphate. After evaporation of the solvent, 29 g of crude product were obtained. This was stirred for 1 hour with a mixture of 190 ml tetrahydrofuran and 50 ml of concentrated hydrochloric acid in order to cleave the acetal. The product was diluted with saturated sodium chloride solution, and the phases were separated, extracted with ether and dried. After removal of the solvent by distillation, compound (8) which was obtained was purified with diisopropyl ether via a silica gel column.

Provenance & Evidence