Water → 4-Chloro-3-methoxybenzoic acid

HRID 2104249Notes

Reaction equation

HRID 2104249 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[O:9][CH3:10].[O-:11][Mn](=O)(=O)=O.[K+].[OH2:17]>[N+](CCCC)(CCCC)(CCCC)CCCC.[Cl-]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:11])=[O:17])=[CH:4][C:3]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 993521-Chloro-2-methoxy-4-methylbenzeneHCID 516875Potassium Permanganate

Product 1

HCID 20633784-Chloro-3-methoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 70681Tetrabutylammonium ChlorideCatalyst

Procedure

2-chloro-5-methylanisole (31.2 g, 1 equiv) and Bu4NCl (2 g, cat.) in 500 mL of water was treated with 95 g of KMnO4 at reflux for 3 hours. The mixture was then filtered through celite, acidified with conc. HCl and the white solid was collected after filtration and air dry to give 4-chloro-3-methoxybenzoic acid.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe mixture was then filtered through celite
  3. customthe white solid was collected
  4. filtrationafter filtration and air
  5. customdry

Sources & evidence

ORD record
ord-bc674fae0739438cb2525a65f17f9ca5
Source dataset
uspto-grants-2009_08
Patent number
US07576218B2

Reaction notes

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