Dimethylformamide → 2-Hydroxy-4-methoxybenzoyl chloride

HRID 639930

Reaction equation

HRID 639930 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].S(Cl)([Cl:15])=O.CN(C=O)C>C(Cl)Cl>[OH:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([Cl:15])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 752314-Methoxysalicylic Acid

Product 1

HCID 231185592-Hydroxy-4-methoxybenzoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-hydroxy-4-methoxybenzoic acid (20 g, 118.9 mmol) in 500 mL CH2Cl2 was added thionyl chloride (21.2 g, 178.4 mmol), followed by 0.4 mL DMF. After stirring at rt for 8 h, the reaction mixture was concentrated to a white solid (azeotroped twice from benzene). This material was used as is in the next step.

Workup

  1. concentrationthe reaction mixture was concentrated to a white solid (
  2. customazeotroped twice from benzene)

Sources & evidence

ORD record
ord-ecf2ec74ab534a90a544406e79f18c91
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Linked notes

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