Water → HCID 59289838, compound

HRID 1496838Notes

Reaction equation

HRID 1496838 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.[CH3:19][CH:20]([CH3:24])[CH2:21][CH2:22]O.OS(O)(=O)=O.O>C(Cl)(Cl)Cl>[CH3:19][CH:20]([CH3:24])[CH2:21][CH2:22][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

6

Reactant 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 31260Isoamyl AlcoholHCID 44140052HCID 44140052, compound

Product 1

HCID 59289838HCID 59289838, compoundYield 23.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

10 g (0.04 mol) of 2-benzoyl-2-hydroxy-cyclohexanecarboxylic acid (of example 1), 7.05 mol 3-methyl-butan-1-ol and 0.5 g H2SO4 are dissolved in 200 ml CHCl3 and heated to reflux during 18 hours using a water separator to remove the water formed during the reaction. The reaction mixture is then cooled to room temperature, washed with sodium bicarbonate and water and dried over Mg2SO4. After distillation of the solvent, the crude reaction product is purified by flash chromatography (silica gel, eluant petroleum ether/ethyl acetate 1:1) to give 3 g 2-benzoyl-2-hydroxy-cyclohexanecarboxylic acid 3-methyl-butyl ester as a colorless liquid.

Workup

  1. temperatureheated
  2. temperatureto reflux during 18 hours
  3. customto remove the water
  4. customformed during the reaction
  5. washwashed with sodium bicarbonate and water
  6. dry with materialdried over Mg2SO4
  7. distillationAfter distillation of the solvent
  8. customthe crude reaction product
  9. customis purified by flash chromatography (silica gel, eluant petroleum ether/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-af2dea58a0b64df69eb1f0c9e6defe4c
Source dataset
uspto-grants-2015_12
Patent number
US09199934B2

Reaction notes

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