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

HRID 2203294Notes

Reaction equation

HRID 2203294 reaction equation
[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH2:14][OH:15])([CH3:4])([CH3:3])[CH3:2]>[O-2].[Mn+4].[O-2].C(Cl)Cl>[C:1]([O:5][C:6](=[O:16])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[CH:14]=[O:15])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 15292992tert-Butyl [2-(hydroxymethyl)phenyl]carbamate

Product 1

HCID 11287472tert-Butyl (2-formylphenyl)carbamate

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

(2-Hydroxymethyl-phenyl)-carbamic acid tert-butyl ester (44.7 g, 0.200 mol), CH2Cl2 (625 mL) and manganese(IV) oxide (85%, 5 μm powder; 245.5 g, 2.400 mol) were introduced into a flask. The mixture was stirred at 40° C. for at least 4 h or until HPLC analysis showed that the reaction had proceeded to greater than 97% completion. The cooled mixture was filtered through a Celite pad (22 g) and the filter cake was rinsed with CH2Cl2 (625 mL). The filtrate and wash were concentrated in vacuo to dryness to afford the title compound as an oily yellow material (44 g, 99% yield).

Workup

  1. filtrationThe cooled mixture was filtered through a Celite pad (22 g)
  2. washthe filter cake was rinsed with CH2Cl2 (625 mL)
  3. washThe filtrate and wash
  4. concentrationwere concentrated in vacuo to dryness

Sources & evidence

ORD record
ord-966054003d6a4fd2b02d8b497925b030
Source dataset
uspto-grants-2016_06
Patent number
US09365575B2

Reaction notes

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