Hydrochloric Acid → 3-(Methoxycarbonyl)-4-methylbenzoic acid

HRID 2071149Notes

Reaction equation

HRID 2071149 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=[O:2].[OH:14]OS([O-])=O.[K+].O.Cl>CN(C=O)C.CCOC(C)=O>[CH3:11][O:10][C:8]([C:7]1[CH:12]=[C:3]([CH:4]=[CH:5][C:6]=1[CH3:13])[C:1]([OH:14])=[O:2])=[O:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 19700886Methyl 5-formyl-2-methylbenzoateHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 220698023-(Methoxycarbonyl)-4-methylbenzoic acid

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 268 mg of the methyl 5-formyl-2-methylbenzoate and 1.08 g (1.76 mmol) of Oxone in 6 mL of DMF was stirred at r.t. for 16.75 h. Water, 1N HCl, and EtOAc were added, and the aqueous layer was extracted with EtOAc. The combined extracts were dried over Na2SO4, filtered, and concentrated, and 3-(methoxycarbonyl)-4-methylbenzoic acid, which was used for the next reaction without further purification.

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialThe combined extracts were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custom3-(methoxycarbonyl)-4-methylbenzoic acid, which was used for the next reaction without further purification

Sources & evidence

ORD record
ord-430dedf4208244fc83ed6b0850c8dd3a
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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