tert-butyl N-[4-(hydroxymethyl)-2-methylphenyl]carbamate → 4-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-methylbenzaldehyde

HRID 844871Notes

Reaction equation

HRID 844871 reaction equation
[CH3:1][C:2]([CH3:17])([O:4][C:5]([NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][OH:13])=[CH:10][C:9]=1[CH3:16])=[O:6])[CH3:3]>ClCCl.[O-2].[O-2].[Mn+4]>[CH3:3][C:2]([CH3:17])([O:4][C:5]([NH:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][C:9]=1[CH3:16])=[O:6])[CH3:1]

Participants

4

Reactant 1

HCID 22981315tert-butyl N-[4-(hydroxymethyl)-2-methylphenyl]carbamate

Product 1

HCID 226137184-[[(1,1-Dimethylethoxy)carbonyl]amino]-3-methylbenzaldehydeYield 77.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-[(1,1-dimethylethoxy)carbonyl]amino-3-methylbenzyl alcohol (42.9 mmol, 10.18 g) in dichloromethane (85 mL) was added manganese dioxide (138 mmol, 12 g) and 4A molecular sieves (6 g) at room temperature. The reaction mixture was stirred for 76 h at room temperature and was filtered through a pad of celite washing with dichloromethane. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel chromatography using a Biotage (40m) column to obtain 7.82 g (77% yield) of 4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methylbenzaldehyde as a white solid: mp 109-111° C. EI-HRMS m/e calcd for C13H17NO3 (M+) 235.1208, found 235.1207.

Workup

  1. filtrationwas filtered through a pad of celite
  2. washwashing with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a4d1c794d7a845eb9e6cb2b2107b8bcb
Source dataset
uspto-grants-2002_04
Patent number
US06380387B1

Reaction notes

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