Veratric Acid → Veratroyl chloride

HRID 1729204Notes

Reaction equation

HRID 1729204 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6](O)=[O:7].S(Cl)([Cl:16])=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([Cl:16])=[O:7]

Participants

3

Reactant 2

HCID 7121Veratric AcidHCID 24386Thionyl Chloride

Product 1

HCID 77070Veratroyl chloride

Procedure

20 g (0.1 mole) of 3,4-dimethoxybenzoic acid are suspended in 170 ml of thionyl chloride and refluxed for 2 hours. The solution is concentrated under reduced pressure. The residual oil crystallizes immediately after the addition of petroleum ether. The crystals are spun and washed with petroleum ether.

Workup

  1. temperaturerefluxed for 2 hours
  2. concentrationThe solution is concentrated under reduced pressure
  3. customThe residual oil crystallizes immediately
  4. additionafter the addition of petroleum ether
  5. washwashed with petroleum ether

Sources & evidence

ORD record
ord-5660d142a34d4b3b94c00e8d12de5dfa
Source dataset
uspto-grants-1994_07
Patent number
US05332735

Reaction notes

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