Iodine → 18-(Benzyloxy)octadecan-9-ol

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%).

1. temperatureThe reaction was warmed to room temperature
2. stirringstirring
3. waitwas continued for another 2 h
4. customThe reaction was quenched with ammonium chloride solution
5. extractionextracted with EtOAc (3×50 ml)
6. washthe combined organic layers were washed with brine solution
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customThe crude product was purified by silica gel column (12% EtOAc in Hexane)

ORD record

ord-90b75d40121142649a757e88d7cf6472

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09365597B2