2,6-Dimethoxybenzoic Acid → 2,6-Dimethoxybenzoyl chloride

HRID 1649307Notes

Reaction equation

HRID 1649307 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5](O)=[O:6].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH3:13])[C:4]=1[C:5]([Cl:16])=[O:6]

Participants

4

Reactant 2

HCID 151092,6-Dimethoxybenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 748102,6-Dimethoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 8.5 Kg portion of 2,6-dimethoxybenzoic acid was dissolved in 60 liters of toluene and the solution was stirred at ambient temperature while 6.8 liters of thionyl chloride was added dropwise over forty-five minutes. Following the addition, the reaction mixture next was cooled to room temperature and the solvent was removed by evaporation under reduced pressure, washed with 25 liters of Pet. ether cooled and filtered to provide a crude solid product. The product was stirred for one hour with 25 liters of fresh Pet. ether, and then cooled to 10° C. and filtered to provide 8.94 Kg of 2,6-dimethoxybenzoyl chloride.

Workup

  1. additionwas added dropwise over forty-five minutes
  2. additionthe addition
  3. customthe solvent was removed by evaporation under reduced pressure
  4. washwashed with 25 liters of Pet. ether
  5. temperaturecooled
  6. filtrationfiltered
  7. customto provide a crude solid product
  8. temperaturecooled to 10° C.
  9. filtrationfiltered

Sources & evidence

ORD record
ord-bcdedd6e6c374ec2b443ded6972fdf57
Source dataset
uspto-grants-1983_11
Patent number
US04416683

Reaction notes

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