tert-Butyl [2-(hydroxymethyl)phenyl]carbamate → tert-Butyl (2-formylphenyl)carbamate

HRID 432494Notes

Reaction equation

HRID 432494 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[OH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24]>C(Cl)(Cl)Cl>[CH:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:12]

Participants

4

Reactant 2

HCID 15292992tert-Butyl [2-(hydroxymethyl)phenyl]carbamateHCID 178418287HCID 178418287, compound3×

Product 1

HCID 11287472tert-Butyl (2-formylphenyl)carbamateYield 79.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A 20% dispersion of pyridinium chlorochromate in basic alumina (50 g) was added to a solution of tert-butyl N-[2-(hydroxymethyl)phenyl]carbamate (11.0 g, 0.0493 mol) in anhydrous chloroform and the resulting suspension was stirred under an atmosphere of nitrogen at ambient temperature for 1 hour. Additional 16 g of a 20% dispersion of pyridinium chlorochromate in basic alumina was added and the stirring was continued for 45 min. At this point in time, additional 15 g of of 20% dispersion of pyridinium chlorochromate in basic alumina was added and the stirring was continued for 25 min. The resulting suspension was filtered through a silica gel pad, the filtrate was concentrated under reduced pressure and the residue purified by flash chromatography on silica using ethyl acetate/n-heptane (2:98) as mobile phase to yield tert-butyl N-(2-formylphenyl)carbamate (8.67 g, 0.0392 mol) as a white solid.

Workup

  1. waitthe stirring was continued for 45 min
  2. waitthe stirring was continued for 25 min
  3. filtrationThe resulting suspension was filtered through a silica gel pad
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue purified by flash chromatography on silica

Sources & evidence

ORD record
ord-98c91750bccf4a45af433d50524393fb
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

Loading…