Hydrochloric Acid → 2-Chloro-4-methoxybenzoic acid

HRID 602312Notes

Reaction equation

HRID 602312 reaction equation
F[C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1.[CH3:12][O-:13].[Na+].Cl>>[CH3:12][O:13][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([Cl:11])[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 752592-Chloro-4-fluorobenzoic acidHCID 10942334Sodium Methoxide

Product 1

HCID 126480262-Chloro-4-methoxybenzoic acid

Procedure

4-fluoro-2-chloro-benzoic acid (10 g) was combined with sodium methoxide (393 mL, 4.37 M in methanol) and heated at 75 C for 46 h. The reaction was cooled to room temp and acidified with 1 N HCl. The mixture was extracted with EtOAc (3×). The combined extracts were then dried (MgSO4) and concentrated to give 8.5 g of 4-methoxy-2-chloro-benzoic acid as a white solid.

Workup

  1. temperatureheated at 75 C for 46 h
  2. extractionThe mixture was extracted with EtOAc (3×)
  3. dry with materialThe combined extracts were then dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7ae61d892c8b41ae92ad11a519e9ba04
Source dataset
uspto-grants-2011_03
Patent number
US07906521B2

Reaction notes

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