Glycerol → 1,3-Bis(triphenylmethoxy)propan-2-ol

HRID 1694588Notes

Reaction equation

HRID 1694588 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]([OH:4])[CH2:5][O:6][C:7]([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)([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

Participants

4

Reactant 2

HCID 753GlycerolHCID 6456Trityl chloride

Product 1

HCID 2250771,3-Bis(triphenylmethoxy)propan-2-olYield 95.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Glycerol (5.0 g, 54.28 mmol) was dried by coevaporations with dry pyridine and dissolved in the same solvent (100 mL). Trityl chloride (45 g, 0.16 mol) was added portionwise, and the mixture was stirred overnight at RT. All volatiles were removed in vacuo. The residue was dissolved in dichloromethane, washed twice with sat NaHCO3 and dried over Na2SO4. Precipitation from diethyl ether gave the title compound (30 g). 1H NMR (CDCl3): 7.40-7.22 (30H) 3.94 (1H, m); 3.29 (4H, m); 2.29 (1H, d, J 5.9). ESI-TOF MS: required for C41H36NaO3+599.26 (M+Na+), found 599.21.

Workup

  1. customAll volatiles were removed in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed twice with sat NaHCO3
  4. dry with materialdried over Na2SO4
  5. customPrecipitation from diethyl ether

Sources & evidence

ORD record
ord-08c16a7dc25c44bba3ec9a6524a5881e
Source dataset
uspto-grants-2012_04
Patent number
US08158782B2

Reaction notes

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