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

HRID 2203294Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2203294
[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]

Komponenten

4

Edukt 1

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

Produkt 1

HCID 11287472tert-Butyl (2-formylphenyl)carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

(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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-966054003d6a4fd2b02d8b497925b030
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09365575B2

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