3,5-Dimethoxybenzoic Acid → 3,5-Dimethoxybenzoyl chloride

HRID 1381882Notes

Reaction equation

HRID 1381882 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6](O)=[O:7].S(Cl)([Cl:16])=O>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6]([Cl:16])=[O:7]

Participants

5

Reactant 2

HCID 143323,5-Dimethoxybenzoic AcidHCID 24386Thionyl Chloride

Product 1

HCID 870033,5-Dimethoxybenzoyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolvent

Procedure

72.9 g of 3,5-dimethoxybenzoic acid are suspended in 320 ml of toluene, and 2 drops of dimethylformamide are added thereto. The suspension is heated to 50°. 40 ml of thionyl chloride are added dropwise at that temperature within a period of 10 minutes. The whole is then heated to 90° (vigorous evolution of gas) and stirred for 2 hours. The reaction mixture is cooled and concentrated by evaporation in a rotary evaporator. After the addition of toluene, the whole is again concentrated by evaporation. The oily residue is dried for 15 minutes under a high vacuum. 3,5-dimethoxybenzoyl chloride is thus obtained.

Workup

  1. temperatureThe suspension is heated to 50°
  2. temperatureThe whole is then heated to 90° (vigorous evolution of gas)
  3. temperatureThe reaction mixture is cooled
  4. concentrationconcentrated by evaporation in a rotary evaporator
  5. additionAfter the addition of toluene
  6. concentrationthe whole is again concentrated by evaporation
  7. customThe oily residue is dried for 15 minutes under a high vacuum

Sources & evidence

ORD record
ord-e4d2c00a1a3c43c8872eb182f8702f82
Source dataset
uspto-grants-1989_02
Patent number
US04804661

Reaction notes

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