Methyl 4-(hydroxymethyl)-2-(trifluoromethyl)benzoate → Methyl 4-formyl-2-(trifluoromethyl)benzoate

HRID 467936Notes

Reaction equation

HRID 467936 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][C:5]=1[C:12]([F:15])([F:14])[F:13]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[O:11])=[CH:6][C:5]=1[C:12]([F:13])([F:15])[F:14]

Participants

4

Reactant 1

HCID 57443316Methyl 4-(hydroxymethyl)-2-(trifluoromethyl)benzoate

Product 1

HCID 57443312Methyl 4-formyl-2-(trifluoromethyl)benzoateYield 84.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxymethyl-2-trifluoromethyl-benzoic acid methyl ester (Example I9) (7.15 g) in dichloromethane (150 ml) was added manganese dioxide (25.1 g). The reaction mixture stirred at ambient temperature for 2.5 hours. The reaction mixture was filtered over a plug of silica gel and the filtrate concentrated to give 4-formyl-2-trifluoromethyl-benzoic acid methyl ester (5.98 g), which was used without further purification. 1H-NMR (CDCl3, 400 MHz): 10.11 (s, 1H), 8.25-7.59 (m, 3H), 3.98 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered over a plug of silica gel
  2. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-a733c875d2bf48a18fcee5c33c163168
Source dataset
uspto-grants-2014_01
Patent number
US08623896B2

Reaction notes

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