Dimethylformamide → 2-Hydroxy-4-methoxybenzoyl chloride

HRID 2358311Notes

Reaction equation

HRID 2358311 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>ClCCCl>[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 chlorideYield 99.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-hydroxy-p-anisic acid (0.2 g, 1.2 mmol) in DCE (8 mL) was added thionyl chloride (0.13 mL, 1.8 mmol) and a drop of DMF. After stirring at room temperature for 4.5 h the reaction mixture was concentrated and azeotroped several times with benzene to give the acid chloride 123 as a white solid (222 mg).

Workup

  1. concentrationwas concentrated
  2. customazeotroped several times with benzene

Sources & evidence

ORD record
ord-bfaddc38c3fc471697e8ad06e946ba5b
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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