Glycerol → 3-Trityloxypropane-1,2-diol

HRID 724754

Reaction equation

HRID 724754 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[C:7](Cl)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>N1C=CC=CC=1>[C:7]([O:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

4

Reactant 2

HCID 753GlycerolHCID 6456Trityl chloride

Product 1

HCID 28828273-Trityloxypropane-1,2-diolYield 59%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In 50 ml of pyridine was dissolved 4.6 g (50 mmol) of glycerol followed by addition of 13.9 g (50 mmol) of trityl chloride and the mixture was stirred at ambient temperature overnight. The reaction mixture was then concentrated under reduced pressure and the residue was diluted with water and extracted with ether. The organic layer was washed with water, dried over magnesium sulfate, and concentrated. The residue was purified by column chromatography (silica gel/chloroform-methanol) to provide 9.5 g (59%) of 1-O-tritylglycerol.

Workup

  1. concentrationThe reaction mixture was then concentrated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionextracted with ether
  4. washThe organic layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel/chloroform-methanol)

Sources & evidence

ORD record
ord-33db2a77cdf744d0b4ea3f6b3d48e678
Source dataset
uspto-grants-1998_01
Patent number
US05705188

Linked notes

Loading…