p-Toluenesulfonic acid monohydrate → (S)-4-Benzyloxy-1,2-butanediol

HRID 1168048Notes

Reaction equation

HRID 1168048 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:15][O:14]C(C)(C)[O:12]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][CH2:10][C@H:11]([OH:12])[CH2:15][OH:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12841372(4S)-4-[2-(Benzyloxy)ethyl]-2,2-dimethyl-1,3-dioxolane

Product 1

HCID 9794180(S)-4-Benzyloxy-1,2-butanediolYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (50 ml) were dissolved (S)-4-(2-benzyloxyethyl)-2,2-dimethyl-1,3-dioxolane (2.06 g, 8.73 mmol) and p-toluenesulfonic acid hydrate (1.68 g, 8.8 mmol), and the solution was stirred at room temperature for 24 hours. After removal of methanol in vacuo, aqueous saturated sodium hydrogen carbonate was added to neutralize the solution. The solution was extracted with ethyl acetete and the extract was washed with saturated brine, dried on sodium sulfate, filtered, and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-4-benzyloxy-1,2-butanediol (1.70 g, yield 99%).

Workup

  1. customAfter removal of methanol in vacuo, aqueous saturated sodium hydrogen carbonate
  2. additionwas added
  3. extractionThe solution was extracted with ethyl acetete
  4. washthe extract was washed with saturated brine
  5. customdried on sodium sulfate
  6. filtrationfiltered
  7. customcondensed in vacuo

Sources & evidence

ORD record
ord-abb3a825cdd84ca08224dd91947f7880
Source dataset
uspto-grants-2003_09
Patent number
US06620977B1

Reaction notes

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