Hydrochloric Acid → 3-Benzyl-1,2-dihexadecylglycerol

HRID 2372301Notes

Reaction equation

HRID 2372301 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]([OH:13])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[OH-].[K+].Cl>C1C=CC=CC=1>[CH2:15]([O:12][CH2:11][CH:10]([CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[O:13][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH3:15])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 82131-BromohexadecaneHCID 14797Potassium HydroxideHCID 980723-(Benzyloxy)-1,2-propanediol

Product 1

HCID 105798713-Benzyl-1,2-dihexadecylglycerolYield 138.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-O-Benzylglycerol (9.0 g, 0.05 mole) and 25 g (0.08 mole) of 1-bromohexadecane are dissolved in 50 ml of dry benzene, 8.8 g (0.16 mole) of potassium hydroxide is added to the solution, and the mixture is heated under reflux with stirring for 16 hours. The reaction mixture is neutralized by adding hydrochloric acid then extracted with 50 ml of ethyl acetate. The extract is washed in sequence with 2.5% potassium hydrogen carbonate and water and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure to give 35 g of an oily residue.

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. extractionthen extracted with 50 ml of ethyl acetate
  4. washThe extract is washed in sequence with 2.5% potassium hydrogen carbonate and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent is then distilled off under reduced pressure

Sources & evidence

ORD record
ord-52144b94cbc94597b6129fb218098f11
Source dataset
uspto-grants-1992_03
Patent number
US05098898

Reaction notes

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