Solketal → 1-O-Dodecylglycerol

HRID 1592850

Reaction equation

HRID 1592850 reaction equation
C[C:2]1([CH3:9])[O:6][CH:5]([CH2:7][OH:8])[CH2:4][O:3]1.[OH-].[K+].Br[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[CH2:2]([O:3][CH2:4][CH:5]([OH:6])[CH2:7][OH:8])[CH2:9][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 7528SolketalHCID 81731-BromodecaneHCID 14797Potassium Hydroxide

Product 1

HCID 977741-O-DodecylglycerolYield 71%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent3×

Procedure

Isopropylidineglycerol (solketal, 26.4 g, 0.20 mol) in 60 mL of toluene 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-Bromodecane (50 g, 0.20 mol) in 40 mL of toluene 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.

Workup

  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

Sources & evidence

ORD record
ord-dfa98373e0a642d691415ec076b97ce8
Source dataset
uspto-grants-2007_11
Patent number
US07294621B2

Linked notes

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