Methanol → HCID 59289857, compound

HRID 1496837Notes

Reaction equation

HRID 1496837 reaction equation
[C:1]([C:9]1([OH:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]1[C:15]([OH:17])=[O:16])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[CH:21]1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[CH3:21][O:16][C:15]([CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][C:9]1([C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[OH:18])=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 44140052HCID 44140052, compound

Product 1

HCID 59289857HCID 59289857, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

9.93 g (0.04 mol) of 2-benzoyl-2-hydroxy-cyclohexanecarboxylic acid prepared according to the method of example 1 and 1.4 g of methanol (0.044 mol) are dissolved in 200 ml of dichloromethane. 9.91 g (0.044 mol) dicyclohexylcarbodiimide are added to the solution and the resulting suspension is stirred for 3 hours at room temperature. After this time, no more carboxylic acid is detected by TLC analysis. The reaction mixture is filtered and the solid dicyclohexylurethane is washed with dichloromethane. The organic solution is washed with sodium bicarbonate and water, dried over MgSO2 and evaporated in vacuum. The residual crude product is purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 9:1) to give 7.03 g (71%) 2-benzoyl-2-hydroxy-cyclohexanecarboxylic acid methyl ester as a viscous resin.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe solid dicyclohexylurethane is washed with dichloromethane
  3. washThe organic solution is washed with sodium bicarbonate and water
  4. dry with materialdried over MgSO2
  5. customevaporated in vacuum
  6. customThe residual crude product is purified by chromatography on silica gel (eluant: petroleum ether/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-7dd63eb5d17c42b595149a5a1d9f7e70
Source dataset
uspto-grants-2015_12
Patent number
US09199934B2

Reaction notes

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