Hydrochloric Acid → 4-Chloro-o-anisic acid

HRID 1702937Notes

Reaction equation

HRID 1702937 reaction equation
Cl[C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH3:12][OH:13].CNC.Cl>[Cu].CCOCC.O>[CH3:12][O:13][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 674DimethylamineHCID 887MethanolHCID 57872,4-Dichlorobenzoic Acid

Product 1

HCID 936824-Chloro-o-anisic acid

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2,4-dichlorobenzoic acid (67.4 g), absolute methanol (135 ml), and copper powder (3.37 g) is refluxed for 6-7 hours while introducing gaseous dimethylamine. The reaction mixture is mixed with a large amount of water, acidified with hydrochloric acid, and shaken with ether. The organic layer is washed with water, dried over sodium sulfate, and evaporated to remove the solvent. The residue is washed with isopropyl ether and filtered to give 2-methoxy-4-chlorobenzoic acid (43.6 g) as crystals melting at 139.5° to 141° C.

Workup

  1. temperatureis refluxed for 6-7 hours
  2. washThe organic layer is washed with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customto remove the solvent
  6. washThe residue is washed with isopropyl ether
  7. filtrationfiltered

Sources & evidence

ORD record
ord-39d713d700444777b4f0ca79ed48e214
Source dataset
uspto-grants-1982_09
Patent number
US04350635

Reaction notes

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