Water → Benzene, ((3-methyl-2-butenyl)oxy)-

Participants

Reaction Steps

A mixture of phenol (18.8 g) and sodium hydroxide (8 g) was stirred at 60°-70° in dimethylformamide (162 ml) and water (18 ml) while 1-bromo-3-methylbut-2-ene (VII, R1 =R2 =CH3, Hal=BR) (29.8 g) was added dropwise over 11/2 h. The mixture was stirred at 60° for 4 h after the addition was complete. It was then poured into water (800 ml) and extracted with ether (3 × 300 ml). The ether extract was washed with 10% sodium hydroxide (200 ml) and then with water (3 × 200 ml) before drying over anhydrous sodium sulphate. The solvent was removed in vacuo, and the residue distilled to give 1-phenoxy-3-methylbut-2-ene (2.4 g, yield 75%) as clear liquid b.p. 116°-118°/18 mm. Hg.

Provenance & Evidence