Benzyl Chloride → 3-(Benzyloxy)-1,2-propanediol

HRID 2372299Notes

Reaction equation

HRID 2372299 reaction equation
[OH-].[Na+].C(=[C:6]([CH:8]([CH2:10][OH:11])[OH:9])[OH:7])(C)C.[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O.C(Cl)(=O)C1C=CC=CC=1.C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1>[CH2:12]([O:11][CH2:10][CH:8]([OH:9])[CH2:6][OH:7])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 7503Benzyl ChlorideHCID 14798Sodium HydroxideHCID 9920395Isopropylideneglycerol

Product 1

HCID 980723-(Benzyloxy)-1,2-propanediolYield 46.1%

Reagents, catalysts & solvents 3

HCID 7412Benzoyl chlorideCatalystHCID 124611Benzyltributylammonium bromideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

The 50 ml of a 50% (w/v) sodium hydroxide solution are added 33 g (0.25 mole) of isopropylideneglycerol, 30.25 ml (0.25 mole) of benzyl chloride and 1.38 g (4 millimoles) of benzoyl chloride and 1.38 g (4 millimoles) of benzyltri-n-butylammonium. The mixture is stirred at 100° C. for 5 hours, then cooled to room temperature, diluted with 50 ml of water and extracted with ether. The extract is washed with water and then the solvent is distilled off under reduced pressure. To the residue is added 70 ml of 15% (w/v) sulfuric acid, and the mixture is stirred at 100° C. for 2.5 hours. After cooling, the unreacted material is removed by extraction with petroleum ether, the aqueous layer is neutralized and then extracted with ethyl acetate, and the extract is washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is then distilled off under reduced pressure to give about 21 g of a yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted with ether
  3. washThe extract is washed with water
  4. distillationthe solvent is distilled off under reduced pressure
  5. additionTo the residue is added 70 ml of 15% (w/v) sulfuric acid
  6. stirringthe mixture is stirred at 100° C. for 2.5 hours
  7. temperatureAfter cooling
  8. customthe unreacted material is removed by extraction with petroleum ether
  9. extractionextracted with ethyl acetate
  10. washthe extract is washed with a saturated sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. distillationThe solvent is then distilled off under reduced pressure

Sources & evidence

ORD record
ord-f6fb81a4b2c34bcaad803c800d2b05c5
Source dataset
uspto-grants-1992_03
Patent number
US05098898

Reaction notes

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