4-Hydroxymethyl-n-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)benzamide → 4-formyl-N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)benzamide

HRID 473394Notes

Reaction equation

HRID 473394 reaction equation
[OH:1][CH2:2][C:3]1[CH:25]=[CH:24][C:6]([C:7]([NH:9][C:10]2[CH:19]=[CH:18][C:17]3[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=3[CH:11]=2)=[O:8])=[CH:5][CH:4]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]2[CH:19]=[CH:18][C:17]3[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=3[CH:11]=2)=[O:8])=[CH:24][CH:25]=1)=[O:1]

Participants

4

Reactant 1

HCID 684321204-Hydroxymethyl-n-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)benzamide

Product 1

HCID 425991574-formyl-N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)benzamideYield 96%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the above alcohol (1.891 g, 5.61 mmol) in dichloromethane (35 ml) was added with manganese dioxide (3.905 g, 44.9 mmol), and the mixture was refluxed by heating for 2 hours with stirring. The reaction mixture was filtered through Cerite under reduced pressure, and Cerite was washed with chloroform. The solvent was evaporated, and then the residue was recrystallized to obtain the title compound (1.802 g, 96%) as colorless prisms.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureby heating for 2 hours
  3. filtrationThe reaction mixture was filtered through Cerite under reduced pressure, and Cerite
  4. washwas washed with chloroform
  5. customThe solvent was evaporated
  6. customthe residue was recrystallized

Sources & evidence

ORD record
ord-1a3aa02566f14db98dba6cebcea75012
Source dataset
uspto-grants-2014_01
Patent number
US08633335B2

Reaction notes

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