Hydrochloric Acid → HCID 21388143, compound

Participants

Reaction Steps

Aluminum chloride (100 g, 0.75 mol) was added slowly (30 minutes) to a solution of 4-methyl-3-pentenenitrile (61.7 g, 0.65 mol) in toluene (300 ml) while maintaining the temperature below 10° C. After stirring an additional 4.0 hours at a temperature below 10° C, the mixture was poured onto an ice, water mixture containing 100 ml of 10% hydrochloric acid. The organic layer was washed (10% Na2CO3 then H2O), concentrated and distilled to yield 94.8 g (78.5%) of 4-methyl-4-p-tolylpentanenitrile (3b) which was 91% the para isomer and 9% meta isomer (glc, 20M): bp 129° (1 mm); nD20 1.5145; δTMSCDCl 3 7.13 (s, 4), 2.28 (s, 3) 1.95 (s, 4); 1.28 (s,6).

Provenance & Evidence