Sodium Bicarbonate → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 409485Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 409485
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=[O:19].[Na+]>ClCCl>[CH3:1][O:8][C:9]([CH:10]1[CH2:15][CH2:14][CH:13]([CH2:16][OH:17])[CH2:12][CH2:11]1)=[O:19].[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH:13]([CH:16]=[O:17])[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 516892Sodium BicarbonateHCID 22106763((1r,4r)-4-((Benzyloxy)methyl)cyclohexyl)methanol

Produkt 2

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl esterHCID 186672404-Benzyloxymethyl-cyclohexanecarbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of (4-benzyloxymethyl-cyclohexyl)-methanol (1.40 g, 6 mmol) in dichloromethane (28 mL) is added Dess-Marin reagent (2.53 g, 6 mmol) at 0° C., and the mixture is stirred for 0.5 hour while warming to room temperature. After addition of saturated aqueous NaHCO3, the aqueous layer is extracted with EtOAc. The combined organic layer (dried with MgSO4) is concentrated. The desired product, 4-benzyloxymethyl-cyclohexanecarbaldehyde, is obtained (1.07 g, 79%) after purification using silica gel column chromatography (eluent: EtOAc/hexane).

Aufarbeitung

  1. extractionthe aqueous layer is extracted with EtOAc
  2. dry with materialThe combined organic layer (dried with MgSO4)
  3. concentrationis concentrated

Quellen und Nachweise

ORD-Eintrag
ord-2efa7ba89571432fac85bedb0f55173a
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759365B2

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