1,10-Dibromodecane → HCID 19874510, compound

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[Na].[Br:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]Br>CO>[CH2:8]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][Br:13])=[CH:7][CH:6]=1)[C:9]([CH3:10])=[O:11]

Participants

Procedure

A solution of 4-hydroxyphenyl propan-2-one, ethylene ketal (5.26 g) in methanol at room temperature, was treated with sodium (0.66 g) and allowed to stir for 10 minutes. The resulting solution was then added dropwise over 15 minutes to a solution of 1,10-dibromodecane (9.0 g) in methanol under reflux and the reaction mixture heated for 3 h. The mixture was allowed to cool and the solvent was removed in vacuo. The residue was partitioned between diethylether and water, the organic layer separated, dried (magnesium sulphate), and the solvent removed in vacuo to give an oil which was chromatographed on silica. Elution with chloroform gave 10-(4-acetonylphenoxy)decyl bromide, ethylene ketal (3.0 g) as an oil.