1-Bromododecane → 1-O-Dodecylglycerol

HRID 1737232

반응식

HRID 1737232 반응식
C(=[C:4]([CH:6]([CH2:8][OH:9])[OH:7])[OH:5])(C)C.[OH-].[K+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]>C1(C)C=CC=CC=1>[CH2:24]([O:9][CH2:8][CH:6]([OH:7])[CH2:4][OH:5])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

참가 물질

5

반응물 3

HCID 89191-BromododecaneHCID 14797Potassium HydroxideHCID 9920395Isopropylideneglycerol

생성물 1

HCID 977741-O-Dodecylglycerol수율 71%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

Isopropylideneglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of tolune was added dropwise to a solution of powdered KOH (22.4 g., 0.04 mol) in 150 mL toluene. The resulting mixture was refluxed for 4 hours. 1-Bromododecane (50 g, 0.20 mol) in 40 mL of tolune was then added dropwise, and the solution was refluxed for 10 hours. 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 was refluxed for 16 hours. After cooling, ice-water (150 mL) was added, and the layers were 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.

후처리

  1. temperatureThe resulting mixture was refluxed for 4 hours
  2. temperaturethe solution was refluxed for 10 hours
  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 was refluxed for 16 hours
  10. temperatureAfter cooling
  11. additionice-water (150 mL) was added
  12. customthe layers were separated
  13. extractionThe aqueous layer was extracted with diethyl ether (2×75 mL)
  14. dry with materialThe combined organic fractions were then dried over sodium sulfate
  15. filtrationfiltered
  16. concentrationconcentrated in vacuo
  17. customThe solid residue was recrystallized from MeOH

출처 및 근거

ORD 기록
ord-983ab369fecf4b05a3b6027792dd731a
출처 데이터셋
uspto-grants-1999_10
특허 번호
US05962437

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