Acetic Acid → 5-(3-Methylundecan-2-yl)benzene-1,3-diol

Reaction equation

C[O:2][C:3]1[CH:10]=[C:9]([CH:11]([CH3:22])[CH:12]([CH3:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH:8]=[C:5]([O:6]C)[CH:4]=1.C(O)(=O)C.Br>O>[CH3:22][CH:11]([C:9]1[CH:10]=[C:3]([OH:2])[CH:4]=[C:5]([CH:8]=1)[OH:6])[CH:12]([CH3:21])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

Procedure

A solution of 30.6 g. of 5-(1,2-dimethyldecyl)-resorcinol dimethyl ether in 350 ml. of glacial acetic acid and 150 ml. of 48% hydrogen bromide is refluxed eight hours, then stirred at 25° for 12 hours. The reaction mixture is diluted with water and extracted three times with ether. The combined extracts are washed with saturated aqueous sodium bisulfite and saturated aqueous sodium bicarbonate, dried (MgSO4), concentrated and distilled to give 5-(1,2-dimethyldecyl)resorcinol.