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

HRID 1627687Notes

Reaction equation

HRID 1627687 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-b88dd87d247446b59c2c035c3ff99495
Source dataset
uspto-grants-2014_07
Patent number
US08785643B2

Reaction notes

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