Water → (3S)-2-(1,2-dihydroxyethyl)oxolane-3,4-diol

HRID 1903333Notes

Reaction equation

HRID 1903333 reaction equation
[OH:1][CH2:2][C@@H:3]([C@H:5]([C@@H:7]([C@@H:9]([CH2:11][OH:12])[OH:10])[OH:8])O)[OH:4].S(=O)(=O)(O)O.O>C1(C)C=CC=CC=1>[CH2:11]1[O:12][CH:5]([CH:3]([OH:4])[CH2:2][OH:1])[C@@H:7]([OH:8])[CH:9]1[OH:10]

Participants

5

Reactant 3

HCID 962WaterHCID 1118Sulfuric AcidHCID 5780Sorbitol

Product 1

HCID 103023(3S)-2-(1,2-dihydroxyethyl)oxolane-3,4-diol

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

364 g sorbitol (2 moles), 600 ml toluene and 1 g concentrated sulfuric acid were placed into the equipment described above. The reaction mixture was heated to reflux temperature and 40 ml water (2.2 moles) was collected by azeotropic distillation within 6 hours. The toluene phase was decanted and the sorbitan formed was dissolved in 300 ml DMSO and placed into the reactor together with 3 ml 50% sodium hydroxide.

Workup

  1. temperatureThe reaction mixture was heated
  2. distillationwas collected by azeotropic distillation within 6 hours
  3. customThe toluene phase was decanted

Sources & evidence

ORD record
ord-9e5b572c3cb04b769c4e77f30238976d
Source dataset
uspto-grants-1984_03
Patent number
US04435586

Reaction notes

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