Water → tert-Butyl (4-formylphenyl)carbamate

HRID 1352511Notes

Reaction equation

HRID 1352511 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][OH:15])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].O>N1C=CC=CC=1.[O-2].[O-2].[O-2].[Cr+6]>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]=[O:15])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 962WaterHCID 10242688Boc-4-aminobenzylalcohol

Product 1

HCID 2771821tert-Butyl (4-formylphenyl)carbamateYield 61.1%

Reagents, catalysts & solvents 2

HCID 10219390chromium (VI) trioxideCatalystHCID 1049PyridineSolvent2×

Procedure

Chromium trioxide (2.4 g) is added in portions to pyridine (29 mL) to maintain the temperature between 0°–10° C. A yellow suspension is formed. A solution of (4-hydroxymethylphenyl)carbamic acid tert-butyl ester (1.8 g) in pyridine (29 mL) is added dropwise to the yellow suspension. The reaction mixture is warmed to room temperature and stirred for 30 minutes. The reaction mixture is poured into water and extracted twice with ethyl acetate. The combined organics are washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated under reduced pressure and chromatographed on silica gel (4:1 ethyl acetate/hexane used as eluant) to give 1.09 g product as a white solid. MS: m/z 222 (M+H)+.

Workup

  1. temperatureto maintain the temperature between 0°–10° C
  2. customA yellow suspension is formed
  3. extractionextracted twice with ethyl acetate
  4. washThe combined organics are washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed on silica gel (4:1 ethyl acetate/hexane used as eluant)

Sources & evidence

ORD record
ord-d12d1daa697a45138be8008c8759e5b3
Source dataset
uspto-grants-2007_05
Patent number
US07220768B2

Reaction notes

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