Ethanol → Cyclohexane, 1,1-diethoxy-

HRID 406959Notes

Reaction equation

HRID 406959 reaction equation
[C:1]1(=O)[CH2:6][CH2:5]C[CH2:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(O)C.[CH:22]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])OCC>O>[CH2:30]([O:29][C:22]1([O:26][CH2:27][CH3:28])[CH2:5][CH2:6][CH2:1][CH2:2][CH2:3]1)[CH3:31]

Participants

6

Reactant 4

HCID 702EthanolHCID 6101p-Toluenesulfonic acidHCID 7967CyclohexanoneHCID 31214Ethyl orthoformate

Product 1

HCID 74279Cyclohexane, 1,1-diethoxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a round bottom flask 6 g (6.4 ml) Cyclohexanone, a pinch of p-toluene sulfonic acid and 10 ml absolute ethanol was taken. Stirred the mixture at R.T. for 5 min. Then add to it 18.12 g (20.3 ml) triethyl orthoformate and stir for 3 hr at R.T. Then distilled on rotavapour to get a thick mass. Add to it 30 ml water and extract with (25 ml×ethyl acetate, wash the organic layer with water, dried it by adding sodium sulfate and concentrate it on rotavapour to give a colorless liquid product.

Workup

  1. stirringstir for 3 hr at R.T
  2. distillationThen distilled on rotavapour
  3. customto get a thick mass
  4. extractionextract with (25 ml×ethyl acetate
  5. washwash the organic layer with water
  6. customdried it
  7. additionby adding sodium sulfate
  8. concentrationconcentrate it on rotavapour
  9. customto give a colorless liquid product

Sources & evidence

ORD record
ord-5f08629a6f464cdab8266a708950e8ba
Source dataset
uspto-grants-2014_06
Patent number
US08754207B2

Reaction notes

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