1-Dodecanethiol → 1-Propanol, 3-(dodecylthio)-

Dodecylthiol (5 g) was dissolved in 50 ml of dry N,N-dimethylformamide and 1 g of 60% sodium hydride was added thereto under ice-cooling. The mixture was stirred at room temperature for 1 hour. Further, a solution of 3.45 g of 3-bromopropanol in 10 ml of dry N,N-dimethylformamide was dropwise added thereto under ice-cooling and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into ice, extracted with ether and washed with 1N hydrochloric acid, a saturated aqueous sodium hydrogencarbonate solution and a saturated aqueous sodium chloride solution. The ether layer was dried and concentrated. The resultant mixture was purified by silica gel column chromatography using hexane-ethyl acetate (10:1→3:1) as an eluent to give 6,071 g of 3-dodecylthiopropanol as a colorless powder.

1. temperatureunder ice-cooling
2. temperatureunder ice-cooling
3. stirringthe mixture was stirred at room temperature for 3 hours
4. additionThe reaction mixture was poured into ice
5. extractionextracted with ether
6. washwashed with 1N hydrochloric acid
7. dry with materialThe ether layer was dried
8. concentrationconcentrated
9. customThe resultant mixture was purified by silica gel column chromatography

ORD record

ord-79b2610031994342b09c82defe5574d6

Source dataset

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05719176