N-(1-hydroxymethyl-2-methyl-propyl)-4-methyl-benzamide → N-(1-formyl-2-methyl-propyl)-4-methyl-benzamide

HRID 1793641Notes

Reaction equation

HRID 1793641 reaction equation
C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O.[OH:12][CH2:13][CH:14]([NH:18][C:19](=[O:27])[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)[CH:15]([CH3:17])[CH3:16]>C(Cl)Cl.CCOCC>[CH:13]([CH:14]([NH:18][C:19](=[O:27])[C:20]1[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=1)[CH:15]([CH3:17])[CH3:16])=[O:12]

Participants

5

Reactant 2

HCID 22022849N-(1-hydroxymethyl-2-methyl-propyl)-4-methyl-benzamideHCID 178418287HCID 178418287, compound

Product 1

HCID 22022850N-(1-formyl-2-methyl-propyl)-4-methyl-benzamideYield 34.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of PCC in 20 mL of CH2Cl2 was added N-(1-hydroxymethyl-2-methyl-propyl)-4-methyl-benzamide (2.2 g, 10 mmol) in 15 mL of CH2Cl2. After the mixture was stirred for 1.5 h, it was diluted with Et2O and filtered through a celite bed. The filtrate was concentrated and the residue purified on a silica gel column with 20% EtOAc in hexane to give 0.75 g of N-(1-formyl-2-methyl-propyl)-4-methyl-benzamide as a white solid (M++1: 220).

Workup

  1. filtrationfiltered through a celite bed
  2. concentrationThe filtrate was concentrated
  3. customthe residue purified on a silica gel column with 20% EtOAc in hexane

Sources & evidence

ORD record
ord-ae678e9bb372491a819577284c2f7716
Source dataset
uspto-grants-2006_07
Patent number
US07081531B2

Reaction notes

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