Veratric Acid → Veratroyl chloride

HRID 2397926Notes

Reaction equation

HRID 2397926 reaction equation
[C:1]([OH:13])(=O)[C:2]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[C:4]([O:5][CH3:6])[CH:3]=1.S(Cl)([Cl:16])=O>C1C=CC=CC=1>[CH3:6][O:5][C:4]1[CH:3]=[C:2]([CH:11]=[CH:10][C:7]=1[O:8][CH3:9])[C:1]([Cl:16])=[O:13]

Participants

4

Reactant 2

HCID 7121Veratric AcidHCID 24386Thionyl Chloride

Product 1

HCID 77070Veratroyl chloride

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Veratric acid (3,4-dimethoxybenzoic acid) (25 g) was suspended in dry benzene (400 ml) and treated with a large excess of thionyl chloride. This mixture was refluxed for 5 hours. The benzene was removed in vacuo and the oily residue was washed 5 times with 150 ml portions of fresh dry benzene followed by distillation of the benzene to remove excess thionyl chloride. This yielded 26.5 g of the desired acid chloride as a light brown solid, m.p. 68°-69° C. (lit. value, 70° C.).

Workup

  1. temperatureThis mixture was refluxed for 5 hours
  2. customThe benzene was removed in vacuo
  3. washthe oily residue was washed 5 times with 150 ml portions of fresh dry benzene
  4. distillationfollowed by distillation of the benzene
  5. customto remove excess thionyl chloride
  6. customThis yielded 26.5 g of the desired acid chloride as a light brown solid, m.p. 68°-69° C. (lit. value, 70° C.)

Sources & evidence

ORD record
ord-1ba343b9e087442297772404e26cb5fe
Source dataset
uspto-grants-1977_05
Patent number
US04022900

Reaction notes

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