Water → (S)-2-(3,3-Diphenyl-2-propenyl)-2-ethylcyclohexanone

Participants

Reaction Steps

A solution of (S)-6-ethyl-α,α-diphenyl-1,4-dioxaspiro[4.5]decane-6-propanol (175 g) in 1 L of acetic acid containing 50 mL of water was refluxed for 3.5 hours. Most of the acetic acid was removed on a rotary evaporator, and the oily residue was poured into 300 mL of water. It was extracted with ether (2×300 mL) and the extracts were combined. They were washed with 1M sodium hydroxide (2×150 mL, first wash neutral, second wash basic) and brine (300 mL). Concentration afforded 140 g of cloudy brown oil.

Provenance & Evidence