Phenol → 8-Phenoxy-1,4-dioxaspiro[4.5]decane

Participants

Reaction Steps

440 mg of 60% sodium hydride in mineral oil (0.12 mmole) were stirred in 9 ml absolute dimethylformamide under a nitrogen atmosphere. 1.1 g (0.12 mmole) phenol were added, followed by 3.1 g (10 mmole) toluene-4-sulphonic acid-1,4-dioxaspiro[4.5]dec-8-yl ester (Gray et al., J. Org. Chem., 35, (1970), 1525-1533), dissolved in 6 ml dimethylformamide. The batch was stirred for 2 hours at a temperature between 80° C. and 85° C. After cooling, the batch was poured on to ice and extracted with ether, and the solution was washed with dilute aqueous sodium hydroxide solution and dried over sodium sulphate. After evaporating off the solvent, the crude product was purified with diisopropyl ether via a silica gel column. 1.27 g (54% theoretical) of compound (25) were obtained as an oil.

Provenance & Evidence