Water → 1-Heptyn-1-ylbenzene

Participants

Reaction Conditions

Reaction Steps

Brown's chromic acid reagent (133 mL, 88 mmol, 0.66 M) was added slowly in drops to a magnetically stirred solution of 7-phenylhept-6-yn-1-ol (6) (7.53 g, 40 mmol) in acetone (400 mL) at 0° C. After the chromic acid had been added, the reaction mixture was stirred for 1 hour at 0° C. and then at room temperature until all the base material has been converted as indicated by TLC. Water (300 mL) was added and the aqueous phase was then extracted with petroleum ether (boiling point 40-60° C.)/Et2O 1:1 (6×50 mL). The combined organic phases were washed with water (2×25 mL) and dried (MgSO4). Distillation on a rotary evaporator yielded 7.3 g (90%) of a pale yellow viscous oil, which crystallized when left to rest. TLC and NMR indicated a pure product.

Provenance & Evidence