2,3-Dimethyl-p-anisaldehyde → 4-Methoxy-2,3-dimethylbenzoic acid

HRID 1037753Notes

Reaction equation

HRID 1037753 reaction equation
[CH3:1][C:2]1[C:9]([CH3:10])=[C:8]([O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].P([O-])(O)(O)=[O:14].[Na+].Cl([O-])=O.[Na+]>CS(C)=O.O>[CH3:12][O:11][C:8]1[CH:7]=[CH:6][C:3]([C:4]([OH:14])=[O:5])=[C:2]([CH3:1])[C:9]=1[CH3:10]

Participants

6

Reactant 3

HCID 5960582,3-Dimethyl-p-anisaldehydeHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphate

Product 1

HCID 134400814-Methoxy-2,3-dimethylbenzoic acidYield 98.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

60.0 g of 2,3-dimethyl-4-methoxybenzaldehyde (DI) are dissolved in 1.20 l of dimethyl sulfoxide. A solution of 131.5 g of sodium dihydrogenphosphate and 132.2 g of sodium chlorite in 480 ml of water is subsequently added dropwise, during which the temperature of the reaction batch is kept below 40° C. The reaction mixture is then stirred at room temperature for a further 2 hours. For work-up, the suspension is diluted with 2.0 l of water and stirred for a further hour. The resultant precipitate is filtered, washed with water and dried at 100° C. in vacuo, giving 65.0 g of the title compound as colourless solid having a melting point of 214° C. (MS: 181.2 (MH+)).

Workup

  1. customis kept below 40° C
  2. stirringstirred for a further hour
  3. filtrationThe resultant precipitate is filtered
  4. washwashed with water
  5. customdried at 100° C. in vacuo

Sources & evidence

ORD record
ord-b91124c4939d4ff0bde51371473b5a58
Source dataset
uspto-grants-2013_10
Patent number
US08546613B2

Reaction notes

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