Thionyl Chloride → 2,3-Diacetoxypropanoyl chloride

HRID 1645492Notes

Reaction equation

HRID 1645492 reaction equation
S(Cl)([Cl:3])=O.[C:5]([O:8][CH:9]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[C:10](O)=[O:11])(=[O:7])[CH3:6]>CN(C)C=O>[C:5]([O:8][CH:9]([CH2:13][O:14][C:15](=[O:17])[CH3:16])[C:10]([Cl:3])=[O:11])(=[O:7])[CH3:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 147372062,3-Diacetoxypropanoic acid

Product 1

HCID 189602932,3-Diacetoxypropanoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Thionyl chloride (62 ml, 0.86 mole) was added dropwise to 2,3-diacetoxypropanoic acid (14) in a flask to which a drop of N,N-dimethylformamide had been added. The mixture was then stirred at ambient temperature over night and then evaporated to a syrup at a temperature ≦40° C. The syrup was taken up in diethyl ether (60 ml) and activated charcoal (0.3 g) added. The mixture was then filtered through a tight glass filter and evaporated in vacuo (10 torr). The oily residue was distilled in a Kugelrohr apparatus to give 24.6 g (68%). Identity and purity checked by 1HNMR in CDCl3.

Workup

  1. additionhad been added
  2. customevaporated to a syrup at a temperature ≦40° C
  3. additionactivated charcoal (0.3 g) added
  4. filtrationThe mixture was then filtered through a tight glass
  5. filtrationfilter
  6. customevaporated in vacuo (10 torr)
  7. distillationThe oily residue was distilled in a Kugelrohr apparatus
  8. customto give 24.6 g (68%)

Sources & evidence

ORD record
ord-82fc11cb2b2e40e68d7ae771d8346819
Source dataset
uspto-grants-2012_02
Patent number
US08124806B2

Reaction notes

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