3,3,3-trifluoro-N-(2-(hydroxymethyl)-4-methoxyphenyl)propanamide → 3,3,3-trifluoro-N-(2-formyl-4-methoxyphenyl)propanamide

HRID 2201495Notes

Reaction equation

HRID 2201495 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH2:15][OH:16])=[O:5]>C(Cl)Cl.O=[Mn]=O>[F:1][C:2]([F:17])([F:18])[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[CH:15]=[O:16])=[O:5]

Participants

4

Reactant 1

HCID 669800523,3,3-trifluoro-N-(2-(hydroxymethyl)-4-methoxyphenyl)propanamide

Product 1

HCID 866899383,3,3-trifluoro-N-(2-formyl-4-methoxyphenyl)propanamideYield 84.9%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3,3,3-trifluoro-N-(2-(hydroxymethyl)-4-methoxyphenyl)propanamide (6.30 g, 23.9 mmol) in anhydrous CH2Cl2 (200 mL) was added MnO2 (20.0 g, 229 mmol). The mixture was refluxed for 16 hours. The mixture was filtered off and the filtrate was concentrated to give the product (5.30 g, yield 84%).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. filtrationThe mixture was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-ad9cbe4b2b9546fba922a4a0f58cebb3
Source dataset
uspto-grants-2016_06
Patent number
US09364481B2

Reaction notes

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