Glycerol → Solketal

HRID 2358324Notes

Reaction equation

HRID 2358324 reaction equation
[OH:1][CH2:2][CH:3]([CH2:5][OH:6])[OH:4].O.[C:8]1(C)[CH:13]=CC(S(O)(=O)=O)=C[CH:9]=1>CC(C)=O>[CH3:9][C:8]1([CH3:13])[O:4][CH:3]([CH2:5][OH:6])[CH2:2][O:1]1

Participants

4

Reactant 2

HCID 753GlycerolHCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 7528SolketalYield 6,265.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a pear-shaped flask equipped with a calcium tube, a condenser, and a Dean-Stark trap, 100 g of glycerine, 300 ml of acetone, 3 g of p-toluenesulfonic acid monohydrate, and 300 ml of petroleum ether were placed, and heated to reflux in an oil bath set at 50° C. After 12 hours, when about 23 ml of water was collected and no further formation of water was confirmed, the reaction mixture was cooled to room temperature. 3 g of sodium acetate was added, and the mixture was stirred for 30 minutes. Petroleum ether and acetone were distilled off in an evaporator. The resulting crude product was purified by vacuum distillation to give 130.6 g of 2,3-O-isopropylideneglycerol in the form of colorless, transparent liquid at 91% yield. 1H-NMR spectral data are shown below:

Workup

  1. customIn a pear-shaped flask equipped with a calcium tube, a condenser
  2. temperatureheated
  3. temperatureto reflux in an oil bath
  4. customset at 50° C
  5. customwhen about 23 ml of water was collected
  6. addition3 g of sodium acetate was added
  7. distillationPetroleum ether and acetone were distilled off in an evaporator
  8. distillationThe resulting crude product was purified by vacuum distillation

Sources & evidence

ORD record
ord-a7c966416bf4447cab4f6e905dc9e731
Source dataset
uspto-grants-2010_07
Patent number
US07763694B2

Reaction notes

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