Texanol → 1-Isobutyryloxy-2,2,4-trimethylpentane-3-yl para-toluenesulfonate

Participants

Reaction Conditions

Reaction Steps

Into a one-liter, four-necked, round bottom flask equipped with stirrer, condenser, and thermometer, 200.0 parts of pyridine and 54.0 parts of 3-hydroxy-2,2,4-trimethylpentyl 2-methylpropionate were mixed under a nitrogen blanket and cooled to 0° C. using an ice water bath. To this, 57.0 parts of para-toluenesulfonyl chloride were added in portions over a thirty minute period. The solution was stirred for one hour at 0° C. and then allowed to stand for twenty-four hours at 15° C. The mixture was subsequently poured into one liter of ice water, which was then extracted with 700 parts of methylene chloride. The organic layer was washed successively with cold 6N sulfuric acid (until the water layer was acidic to pH paper); dilute sodium bicarbonate (three times with 500 part-portions); and water (twice with 500 part-portions). It was then dried over sodium sulfate, filtered, and the solvent removed in vacuo to yield the 1-isobutyryloxy-2,2,4-trimethylpentane-3-yl para-toluenesulfonate.

Provenance & Evidence