2,4,5-Trimethoxybenzoic acid → 2,4,5-Trimethoxybenzoyl chloride

HRID 1106445

Reaction equation

HRID 1106445 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:4]=1[C:5](O)=[O:6].S(Cl)([Cl:18])=O>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]([O:14][CH3:15])=[CH:8][C:4]=1[C:5]([Cl:18])=[O:6]

Participants

4

Reactant 2

HCID 102762,4,5-Trimethoxybenzoic acidHCID 24386Thionyl Chloride

Product 1

HCID 27608092,4,5-Trimethoxybenzoyl chlorideYield 89.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 2,4,5-trimethoxybenzoic acid (2.12 g, 10 mmol) in dry 10 mL benzene was added thionyl chloride (4.4 mL, 60 mmol). The reaction mixture was stirred at 70° C. for 5 hr. The solvent was evaporated in vacuo. The residue was washed with hexane to give 2.07 g of the title compound which was used for the next step without further purification. 1H NMR (CDCl3) δ: 7.65 (1 H, s), 6.50 (1 H, s), 4.05 (3 H, s), 3.97 (3 H, s), 3.86 (3 H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. washThe residue was washed with hexane

Sources & evidence

ORD record
ord-6c4662da3acb424caf91f7c4bb1cc266
Source dataset
uspto-grants-2000_05
Patent number
US06057315

Linked notes

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