Sulfuric Acid → HCID 12702707, compound

Participants

Reaction Steps

A solution of 174.6 parts by weight of cis-4-(trimethylsilyl)-3-buten-2-ol (III) in 2000 parts by volume of acetone is chilled to -10° C. and treated slowly with an excess (350 parts by volume) of Jones Reagent (a solution of chromic acid and sulfuric acid in water) while keeping the internal temperature below 10° C. The resulting precipitate is allowed to settle and the supernatant is decanted and concentrated on a rotary evaporator at 25° C. to remove much of the acetone. The precipitate is dissolved in water and the solution is extracted with ethyl ether. The ether extract is added to the acetone residue and the combined solutions are washed with water, then with 5% aqueous hydrochloric acid, and again with water. The ether extract is then dried over sodium sulfate and the ether removed by vacuum distillation. The residue is taken up in 500 parts by volume of isopropanol and 20 parts by volume of concentrated aqueous hydrochloric acid is added. The mixture is stored at room temperature for 18 hours then diluted with 1000 parts by volume of benzene and washed repeatedly with water. The washes are extracted with 500 parts by volume of benzene and dried over sodium sulfate to yield trans-4-(trimethylsilyl)-3-buten-2-one (IV) which has a boiling point of 165°-169° C. and is represented by the following structural formula ##STR10##

Provenance & Evidence