1-Bromohexadecane → (S)-3-(Hexadecyloxy)propane-1,2-diol

19.4 grams of (R)-(−)-2,2-dimethyl-1,3-dioxolane-4-methanol, 49 grams of powdered KOH and 4.8 grams of hexadecyl bromide were stirred in 500 ml toluene (500 ml) were stirred and refluxed for 6 hours, while removing the water formed by azeotropic distillation. The volume of the solvent was gradually reduced to about 100 ml and the reaction mixture was cooled to room temperature. The cooled reaction mixture was dissolved in 500 ml dichloromethane, washed twice with 200 ml water, and the solvent was removed under reduced pressure. The obtained residue was dissolved in 500 ml of a 90:10:5 (v/v) mixture of methanol:water:concentrated H2SO4, and the resulting solution was refluxed for 30 minutes, cooled to room temperature, and extracted with 500 ml dichloromethane. The extract was washed twice with 100 ml water, 100 ml aqueous 5% sodium carbonate, and again with 100 ml water, until neutral. The solvent was removed under reduced pressure and the crude product was recrystallized from hexane at 4° C., yielding 35.3 grams of pure 1-hexadecyl-sn-glycerol. The yield was 76%.

1. temperaturerefluxed for 6 hours
2. customwhile removing the water
3. customformed by azeotropic distillation
4. customThe cooled reaction mixture
5. washwashed twice with 200 ml water
6. customthe solvent was removed under reduced pressure
7. dissolutionThe obtained residue was dissolved in 500 ml of a 90:10:5 (v/v) mixture of methanol
8. temperaturewater:concentrated H2SO4, and the resulting solution was refluxed for 30 minutes
9. temperaturecooled to room temperature
10. extractionextracted with 500 ml dichloromethane
11. washThe extract was washed twice with 100 ml water, 100 ml aqueous 5% sodium carbonate
12. customThe solvent was removed under reduced pressure
13. customthe crude product was recrystallized from hexane at 4° C.

ORD record

ord-5fe59cf19a15432fbf3599bf07a66edb

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206206B2