1,2-Dibromoethane → HCID 12725189, compound

Reaction equation

[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Br:9])[C:3]=1[OH:10].[Br:11][CH2:12][CH2:13]Br.[OH-].[K+]>C(O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Br:9])[C:3]=1[O:10][CH2:13][CH2:12][Br:11]

Participants

Procedure

A mixture of 2,6-dibromo-4-methylphenol (18) (26.59 g, 0.1 mol), 1,2-dibromoethane (11.2 ml, 0.13 mol) and potassium hydroxide (8.42 g, 0.15 mol) in 200 ml of absolute ethanol was heated under reflux for 24 hours. The inorganic salt was collected on a filter and the filtrate taken to dryness. The resulting mixture was treated with ethyl ether, chilled, and the solid, which proved to be recovered phenol, collected on a filter. The filtrate was evaporated to afford the ether 19 (24.5 g, 65.7%) as a liquid. This was purified by distillation (0.5 torr, 120°-124° C.) to yield 19.79 g (53.0%) of product. NMR (CDCl3) δ 7.25 (s, 2H, aromatic protons), 3.55-4.38 (m, 4H, 2CH2), and 2.27 (s, 3H, CH3).