p-Toluenesulfonic acid monohydrate → 2-benzyloxymethyl-propane-1,3-diol

HRID 1459162Notes

Reaction equation

HRID 1459162 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][O:14]C(C)(C)[O:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([O:8][CH2:9][CH:10]([CH2:15][OH:14])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 23295265HCID 23295265, compound

Product 1

HCID 102417822-benzyloxymethyl-propane-1,3-diolYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-benzyloxymethyl-2,2-dimethyl-1,3-dioxane (3.40 g, 14.4 mmol) and a few crystals of p-toluenesulfonic acid monohydrate in 100 mL of methanol was stirred at room temperature for 20 h. The methanol was removed in vacuo and the residual oil purified by column chromatography on silica gel (ethyl acetate) to give 2.25 g (80%) of 2-benzyloxymethyl-1,3-propanediol as a colorless, clear liquid.

Workup

  1. customThe methanol was removed in vacuo
  2. customthe residual oil purified by column chromatography on silica gel (ethyl acetate)

Sources & evidence

ORD record
ord-a1b0a27d31e5423ca1d9533fd44f2c34
Source dataset
uspto-grants-1998_12
Patent number
US05854228

Reaction notes

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