Water → 1003-85-6

HRID 467296Notes

Reaction equation

HRID 467296 reaction equation
[CH3:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].[S:8](Cl)(Cl)=[O:9].O>C(Cl)Cl>[CH3:1][C:2]1([CH3:7])[CH2:5][O:6][S:8](=[O:9])[O:4][CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 24386Thionyl ChlorideHCID 31344Neopentyl glycol

Product 1

HCID 108772941003-85-6Yield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25.36 g (0.24 mol) of 2,2-dimethylpropane-1,3-diol was suspended at room temperature in 150 ml of methylene chloride in a 500 ml three-necked flask. 37.36 g (0.31 mol) of thionyl chloride was instilled over 30 minutes. After the end of the addition, the reaction solution was held at reflux for 1.5 hours and then cooled to room temperature. 100 ml of water was added to the reaction. The aqueous phase was discarded; the organic phase was extracted three times with saturated NaHCO3 solution (100 ml), then dried with Na2SO4 and concentrated by evaporation on a rotary evaporator. The residue was distilled at 24 mbars and 78° C. The product was a pure colorless liquid according to GC and weighed 23.4 g, which corresponded to a yield of 92 percent.

Workup

  1. additionAfter the end of the addition
  2. temperatureat reflux for 1.5 hours
  3. extractionthe organic phase was extracted three times with saturated NaHCO3 solution (100 ml)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated by evaporation on a rotary evaporator
  6. distillationThe residue was distilled at 24 mbars and 78° C

Sources & evidence

ORD record
ord-92b509c9928a459bbfa1c5331f1933d0
Source dataset
uspto-grants-1992_10
Patent number
US05159100

Reaction notes

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