4-Methoxyphenylacetic Acid → 4-Methoxyphenylacetyl chloride

HRID 2291872Notes

Reaction equation

HRID 2291872 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([OH:12])=O)=[CH:5][CH:4]=1.S(Cl)([Cl:15])=O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([Cl:15])=[O:12])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 76904-Methoxyphenylacetic AcidHCID 24386Thionyl Chloride

Product 1

HCID 27346884-Methoxyphenylacetyl chlorideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
65 °C

Procedure

Thionyl chloride (200 ml) was added to 4-methoxyphenylacetic acid (78 g, 0.47 mole) followed by one drop of dimethylformamide. The reaction was heated at 65° C. for 4 hours and the solvent was removed under vacuum. The residue was distilled in vacuo (water aspirator) at 135° C. to give the product as a red oil (75.9 g, 88%).

Workup

  1. customthe solvent was removed under vacuum
  2. distillationThe residue was distilled in vacuo (water aspirator) at 135° C.

Sources & evidence

ORD record
ord-10634a45803b44b5a2f52bfad6936b74
Source dataset
uspto-grants-1989_01
Patent number
US04798843

Reaction notes

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