Methanol → 4-Benzyloxymethyl-cyclohexanecarboxylic acid methyl ester

HRID 1966073Notes

Reaction equation

HRID 1966073 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-]Cl.[Na+].[CH3:21][OH:22]>C(O)(=O)C>[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

5

Reactant 3

HCID 887MethanolHCID 186672404-Benzyloxymethyl-cyclohexanecarbaldehydeHCID 23665760Sodium Hypochlorite

Product 1

HCID 576866884-Benzyloxymethyl-cyclohexanecarboxylic acid methyl esterYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of (4-benzyloxymethyl-cyclohexyl)-methanol (1.40 g, 6 mmol) in dichloromethane 28 mL is added Dess-Martin periodinate (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 mixture is extracted with EtOAc. The combined organic layer after dried over MgSO4 is concentrated to obtain 4-benzyloxymethyl-cyclohexanecarbaldehyde as clear oil (1.07 g, 79%) after purification. 4-Benzyloxymethyl-cyclohexanecarbaldehyde (1.70 g, 2.0 mmol) is dissolved in acetic acid (0.24 mL) and 2 mL of methanol. The reaction mixture is cooled to 0° C. to 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 mixture is extracted with EtOAc. The combined organic layer after dried over MgSO4 is concentrated to obtain 4-benzyloxymethyl-cyclohexanecarboxylic acid methyl ester as clear oil (343 mg, 65%) after purification.

Workup

  1. customafter purification
  2. temperatureThe reaction mixture is cooled to 0° C. to 5° C.
  3. additionis added dropwise over 20 minutes
  4. customThe cooling bath is removed
  5. customto come to room temperature
  6. additionAfter addition of saturated aqueous NaHCO3
  7. extractionthe mixture is extracted with EtOAc
  8. dry with materialThe combined organic layer after dried over MgSO4
  9. concentrationis concentrated

Sources & evidence

ORD record
ord-ea4dabd9267b4104ad71cce2aae9a9bb
Source dataset
uspto-grants-2013_04
Patent number
US08420641B2

Reaction notes

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