1-Bromododecane → 1-O-Dodecylglycerol

Isopropylideneglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene was added dropwise to a solution of powered KOH (22.4 g, 0.04 mol) in 150 mL of toluene. The resulting mixture was refluxed for 4 h. 1-Bromododecane (50 g, 0.20 mol) in 40 mL of toluene was then added dropwise, and the solution was refluxed for 10 h. After cooling, the reaction mixture was diluted with 200 mL of ice-water and extracted with diethyl ether (3×100 mL). The ether layers were dried over magnesium sulfate, and the solvent was removed in vacuo. The residue was dissolved in 60 mL of diethyl ether and 260 mL of MeOH. Concentrated HCl (60 mL) was added, and the solution refluxed for 16 h. After cooling, ice-water (150 mL) was addecl, and the layers separated. The aqueous layer was extracted with diethyl ether (2×75 mL). The combined organic fractions were then dried over sodium sulfate, filtered, and concentrated in vacuo. The solid residue was recrystallized from MeOH to give 37 g (0.14 mol, 71%) of a white solid.

1. temperatureThe resulting mixture was refluxed for 4 h
2. temperaturethe solution was refluxed for 10 h
3. temperatureAfter cooling
4. extractionextracted with diethyl ether (3×100 mL)
5. dry with materialThe ether layers were dried over magnesium sulfate
6. customthe solvent was removed in vacuo
7. dissolutionThe residue was dissolved in 60 mL of diethyl ether
8. additionConcentrated HCl (60 mL) was added
9. temperaturethe solution refluxed for 16 h
10. temperatureAfter cooling
11. customthe layers separated
12. extractionThe aqueous layer was extracted with diethyl ether (2×75 mL)
13. dry with materialThe combined organic fractions were then dried over sodium sulfate
14. filtrationfiltered
15. concentrationconcentrated in vacuo
16. customThe solid residue was recrystallized from MeOH

ORDレコード

ord-aa812f42e5b945e9ac2fd4e414a1b5d7

出典データセット

uspto-grants-2000_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06030960