Acrolein → 6,6-dimethylhept-1-en-4-yn-3-ol

Participants

Reaction Steps

Ten grams (0.122 mole) of 3,3-dimethyl-1-butyne was dissolved in 100 ml of anhydrous tetrahydrofuran and the resulting solution was cooled to -40° C. or less in a dry ice-acetone bath. Under the stream of a nitrogen gas, 81.13 ml (0.122 mole) of a 1.5M hexane solution of n-butyllithium was added dropwise at -40° C. or less with stirring. After ageing the reaction solution at -50° C. for 30 minutes, 6.84 g (0.122 mole) of acrolein was added dropwise at -50° C. or less. After the reaction solution was allowed to stand overnight at room temperature, it was poured into 200 ml of ice water and extracted with two 100-ml portions of ethyl acetate. The organic layers were combined, washed once with 100 ml of a saturated aqueous sodium chloride solution and concentrated under reduced pressure. The resulting oily product was distilled under reduced pressure to obtain 125 g of 3-hydroxy-6,6-dimethylhept-1 -ene-4-yne (bp20, 80° C.).

Provenance & Evidence