Trifluoroacetic acid methylene chloride → 4-Methoxy-3,5-dimethyl-benzofuran-2-carboxylic acid

HRID 29425Notes

Reaction equation

HRID 29425 reaction equation
C([O:5][C:6]([C:8]1[O:9][C:10]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([O:19][CH3:20])[C:11]=2[C:12]=1[CH3:13])=[O:7])(C)(C)C.C(O)(C(F)(F)F)=O.ClCCl>>[CH3:20][O:19][C:14]1[C:11]2[C:12]([CH3:13])=[C:8]([C:6]([OH:7])=[O:5])[O:9][C:10]=2[CH:17]=[CH:16][C:15]=1[CH3:18]

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 68716639HCID 68716639, compound

Product 1

HCID 687142664-Methoxy-3,5-dimethyl-benzofuran-2-carboxylic acidYield 86.3%

Procedure

To 80 mg of 4-methoxy-3,5-dimethyl-benzofuran-2-carboxylic acid tert-butyl ester was added 2 mL of TFA/dichloromethane (1:1) and the solution was stirred at room temperature for 3 h. When the reaction was done, the solvents were removed under vacuum and the residue was triturated with hexane/dichloromethane. Filtration of the suspension gave 55 mg of 4-methoxy-3,5-dimethyl-benzofuran-2-carboxylic acid as a pale brown solid.

Workup

  1. customthe solvents were removed under vacuum
  2. customthe residue was triturated with hexane/dichloromethane
  3. filtrationFiltration of the suspension

Sources & evidence

ORD record
ord-650a6d34ac2642909462892cf31f4d53
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Reaction notes

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