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

HRID 409485Notes

Reaction equation

HRID 409485 reaction equation
[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

Participants

5

Reactant 2

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

Product 2

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-2efa7ba89571432fac85bedb0f55173a
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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