Iodine → 18-(Benzyloxy)octadecan-9-ol
Reaction equation
II.Br[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.C1C[O:34]CC1>>[CH2:24]([O:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]([OH:34])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1Participants
5
Procedure
To a stirred suspension of Mg metal (0.65 g, 26.83 mmol) and a catalytic amount of Iodine in dry THF (20 ml) at 70° C., 1-bromooctane (3.57 ml, 23.48 mmol) in THF (10 ml) was added dropwise. Stirring was continued for another 30 minutes at this temperature, then the reaction mixture was cooled to room temperature, and was added slowly to a stirred solution of (((10-bromodecyl)oxy)methyl)benzene (4.4 g, 16.77 mmol) in THF (30 ml) at 0° C. The reaction was warmed to room temperature and stirring was continued for another 2 h. The reaction was quenched with ammonium chloride solution, extracted with EtOAc (3×50 ml), the combined organic layers were washed with brine solution, dried over MgSO4 and concentrated. The crude product was purified by silica gel column (12% EtOAc in Hexane) to give 18-(benzyloxy)octadecan-9-ol as a low melting white colored solid (3.85 g, 61%).