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

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.

1. additionafter the addition
2. extractionextracted with ether (3 × 300 ml)
3. extractionThe ether extract
4. washwas washed with 10% sodium hydroxide (200 ml)
5. dry with materialwith water (3 × 200 ml) before drying over anhydrous sodium sulphate
6. customThe solvent was removed in vacuo
7. distillationthe residue distilled

ORD record

ord-eff6766539444b98beccb292ed4590c7

Source dataset

uspto-grants-1977_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04042589