Methanol → Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl ester

HRID 409486Notes

Reaction equation

HRID 409486 reaction equation
[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.[O-:18]Cl.[Na+].[CH3:21][OH:22]>C(O)(=O)C>[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:18].[CH3:21][O:22][C:16]([CH:13]1[CH2:12][CH2:11][CH:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:15][CH2:14]1)=[O:17]

Participants

6

Reactant 3

HCID 887MethanolHCID 186672404-Benzyloxymethyl-cyclohexanecarbaldehydeHCID 23665760Sodium Hypochlorite

Product 2

HCID 11073869Cyclohexanecarboxylic acid, 4-(hydroxymethyl)-, methyl esterHCID 576866884-Benzyloxymethyl-cyclohexanecarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
2.5 °C

Procedure

4-Benzyloxymethyl-cyclohexanecarbaldehyde (1.70 g, 2.0 mmol) is dissolved in acetic acid (0.24 mL) and 2 mL of MeOH. The reaction mixture is cooled to 0-5° C. and stirred while 10% NaOCl solution (2.5 mL, 4 mmol) is added dropwise over 20 minutes. The cooling bath is removed and the mixture is allowed to come 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-cyclohexanecarboxylic acid methyl ester, is obtained (343 mg, 65%) after purification using silica gel column chromatography (eluent: EtOAc/hexane).

Workup

  1. additionis added dropwise over 20 minutes
  2. customThe cooling bath is removed
  3. customto come to room temperature
  4. additionAfter addition of saturated aqueous NaHCO3
  5. extractionthe aqueous layer is extracted with EtOAc
  6. dry with materialThe combined organic layer (dried with MgSO4)
  7. concentrationis concentrated

Sources & evidence

ORD record
ord-d7f62e37ac8f447daf4b1c4c90f52f06
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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