Sulfuric Acid → 6,6-dimethylhept-1-en-4-yn-3-ol

Participants

Reaction Conditions

Reaction Steps

Butyllithium 1.6 M solution in hexane (106.2 ml, 0.17 mole) was added dropwise during 70 minutes to a mixture of t-butylacetylene (13.3 gr., 0.162 mole) and tetrahydrofuran (133.1 ml) at 0° C. A solution of freshly distilled acrolein (10 gr., 0.17 mole) in tetrahydrofuran (26.6 ml) was added to the reaction mixture at 0° C. during 45 minutes. The reaction mixture was stirred at 0° C. for 40 minutes. It was further stirred for 18 hours at room temperature. Saturated ammonium chloride solution (45 ml) was added. The reaction mixture was brought to pH 6 using 10% sulfuric acid (about 85 ml). Tetrahydrofuran was evaporated under reduced pressure. The residue was extracted by dichloromethane. The organic phase was washed with water and dried. The dichloromehane was removed to give the crude product (20.1 gr., 90% yield). Pure 6,6-dimethylhept-1-en-4-yn-3-ol was obtained by distillation. Boiling point was 83° C. at 24 mbar. 13.5 gr. were obtained (60.6% yield).

Provenance & Evidence