Water → HCID 19780713, compound

Participants

Reaction Steps

A solution of the diol (D) (100 mg, 0.45 mM) and p-toluenesulphonic acid (10 mg) in benzene (20 ml) was heated for 1 hour under reflux in an apparatus for the azeotropic removal of water. The reaction solution was cooled, and washed with aqueous sodium hydroxide (2M), followed by brine. The dried (Na2SO4) solution was concentrated in vacuo. The residual oil was purified by flash chromatography, eluting with toluene/hexane (1:1 v/v), to give 2,3,4,5-tetrahydro-2,2,6,8-tetramethyl-1-benzoxepin (E) as a colourless oil (90 mg, 98% yield); NMR: 1.25(6H,s), 1.63(4H,m), 2.23(3H,s), 2.25(3H,s), 2.73(2H,m), 6.57(1H,s), 6.69(1H,s).

Provenance & Evidence