Benzene → 1-O-Hexadecylglycerol

HRID 1464915Notes

Reaction equation

HRID 1464915 reaction equation
C[C:2]1([CH3:9])[O:6][C@H:5]([CH2:7][OH:8])[CH2:4][O:3]1.[OH-].[K+].[CH2:12](Br)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]CC.C1C=CC=CC=1>O>[CH2:2]([O:3][CH2:4][CH:5]([CH2:7][OH:8])[OH:6])[CH2:9][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]

Participants

6

Reactant 4

HCID 241BenzeneHCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 736056(R)-Solketal

Product 1

HCID 727331-O-HexadecylglycerolYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 40 ml (R)-(−)-2,2 dimethyl-1,3-dioxolane-4-methanol, 55 grams of powdered potassium hydroxide and 109 ml hexadecyl bromide were added to 500 ml benzene, and the reaction mixture was stirred and refluxed for 6 hours, while removing the water formed by azeotropic distillation. The volume of the solvent was gradually reduced to about 150 ml. The reaction mixture was then cooled to room temperature and stirred at this temperature overnight. Thereafter, 150 ml water was added, and the obtained mixture was extracted thrice with 150 ml diethyl ether. The combined organic phase was washed with 150 ml water and the solvent was then removed under reduced pressure. The residue was dissolved in 200 ml of a mixture of 90:10:5 (volume/volume) methanol:water:concentrated HCl, and the resulting solution was refluxed for 2 hours. After cooling to room temperature and adding 200 ml water, the product was extracted with 250 ml chloroform. The organic phase was washed consecutively with 250 ml water, 200 ml saturated aqueous solution of sodium carbonate, and again with 200 ml water. The solvent was removed under reduced pressure and the product was then crystallized from hexane (500 ml) to give 81.25 grams (yield 79%) of pure 1-hexadecyl-glycerol, which was dried in a desiccator under reduced pressure.

Workup

  1. temperaturerefluxed for 6 hours
  2. customwhile removing the water
  3. customformed by azeotropic distillation
  4. stirringstirred at this temperature overnight
  5. extractionthe obtained mixture was extracted thrice with 150 ml diethyl ether
  6. washThe combined organic phase was washed with 150 ml water
  7. customthe solvent was then removed under reduced pressure
  8. dissolutionThe residue was dissolved in 200 ml of a mixture of 90:10:5 (volume/volume) methanol
  9. temperaturewater:concentrated HCl, and the resulting solution was refluxed for 2 hours
  10. temperatureAfter cooling to room temperature
  11. additionadding 200 ml water
  12. extractionthe product was extracted with 250 ml chloroform
  13. washThe organic phase was washed consecutively with 250 ml water, 200 ml saturated aqueous solution of sodium carbonate
  14. customThe solvent was removed under reduced pressure
  15. customthe product was then crystallized from hexane (500 ml)

Sources & evidence

ORD record
ord-b5cdd30aff34452692eeeaab88a87680
Source dataset
uspto-grants-2015_04
Patent number
US08999960B2

Reaction notes

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