p-Toluenesulfonic acid → (4,4-Diethoxycyclohexylmethoxymethyl)benzene

HRID 1960028Notes

Reaction equation

HRID 1960028 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:15][CH2:14]C(=O)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:20]([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23])C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(N(CC)CC)C>C(O)C>[CH2:25]([O:24][C:20]1([O:21][CH2:22][CH3:23])[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)[CH3:26]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 31214Ethyl orthoformateHCID 10443381Cyclohexanone, 4-[(phenylmethoxy)methyl]-

Product 1

HCID 57617622(4,4-Diethoxycyclohexylmethoxymethyl)benzene

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Benzyloxymethylcyclohexanone (168 g, 0.77 mol) is dissolved in ethanol (2000 mL), and then triethylorthoformate (350 mL) and p-toluenesulfonic acid (13.3 g) are added. The resulting mixture is stirred and refluxed for 6 hours. After addition of triethylamine (10.5 mL) at room temperature, the mixture is concentrated (500 mL). After addition of sat. NaHCO3 aq., the resulting mixture is extracted with EtOAc. The water layer is extracted with EtOAc and the combined organic layer is washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The crude mixture is purified by short pad silica gel column chromatography to afford (4,4-diethoxycyclohexylmethoxymethyl)benzene.

Workup

  1. temperaturerefluxed for 6 hours
  2. concentrationthe mixture is concentrated (500 mL)
  3. additionAfter addition of sat. NaHCO3 aq.
  4. extractionthe resulting mixture is extracted with EtOAc
  5. extractionThe water layer is extracted with EtOAc
  6. washthe combined organic layer is washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe crude mixture is purified by short pad silica gel column chromatography

Sources & evidence

ORD record
ord-289efcd4649d4d9597efd4258cad4e7e
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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