Glycerol → 3-Trityloxypropane-1,2-diol

HRID 80322Notes

Reaction equation

HRID 80322 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].[C:7]1([C:13]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)Cl)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.O>N1C=CC=CC=1>[OH:1][CH2:2][CH:3]([OH:4])[CH2:5][O:6][C:13]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 753GlycerolHCID 962WaterHCID 6456Trityl chloride

Product 1

HCID 28828273-Trityloxypropane-1,2-diolYield 42.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Glycerol (3.02 g, 32.8 mmol) (Wako Pure Chemical Industries, Ltd.) and triphenylchloromethane (1.00 g, 3.50 mmol) (Wako Pure Chemical Industries, Ltd.) were dissolved in pyridine (20 mL) (Wako Pure Chemical Industries, Ltd.), and the mixture was refluxed for 5 hours. The mixture was allowed to cool to room temperature, and then water was added thereto, followed by extraction with ethyl acetate (Wako Pure Chemical Industries, Ltd.). The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.), and the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography (chloroform (Wako Pure Chemical Industries, Ltd.):methanol (Wako Pure Chemical Industries, Ltd.)=97:3), to thereby obtain the title compound (0.50 g, 42% yield).

Workup

  1. temperaturethe mixture was refluxed for 5 hours
  2. extractionfollowed by extraction with ethyl acetate (Wako Pure Chemical Industries, Ltd.)
  3. dry with materialThe organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.)
  4. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-5cdf62e5d81f4686b4da3b3a65a49966
Source dataset
uspto-grants-2014_09
Patent number
US08846012B2

Reaction notes

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