Ethanol → 3-Ethoxycyclohept-2-en-1-one

HRID 1650060Notes

Reaction equation

HRID 1650060 reaction equation
[C:1]1(=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][C:3](=[O:8])[CH2:2]1.O.[C:11]1(C)C=CC(S(O)(=O)=O)=C[CH:12]=1.C(O)C>C1(C)C=CC=CC=1>[CH2:11]([O:8][C:3]1[CH2:4][CH2:5][CH2:6][CH2:7][C:1](=[O:9])[CH:2]=1)[CH3:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 4072367Cycloheptane-1,3-dione

Product 1

HCID 156706513-Ethoxycyclohept-2-en-1-oneYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 22.3 g. (0.177 mole) of cycloheptan-1,3-dione and 600 mg. (3.16 mmoles) of p-toluenesulfonic acid monohydrate in 86 ml. of ethanol and 250 ml. of toluene was heated at reflux for 18 hours. A soxhlet extractor filled with molecular sieves (3 Å) was used to remove water from the reaction. The reaction was cooled, added to 800 ml. saturated sodium chloride and extracted with four 800 ml. portions of ether. The combined organic extract was dried over magnesium sulfate and evaporated to an oil. Distillation of the crude oil gave 25.3 g. (93%) of the title compound as an oil.

Workup

  1. temperatureat reflux for 18 hours
  2. additionA soxhlet extractor filled with molecular sieves (3 Å)
  3. customto remove water
  4. customfrom the reaction
  5. temperatureThe reaction was cooled
  6. additionadded to 800 ml
  7. extractionsaturated sodium chloride and extracted with four 800 ml
  8. extractionThe combined organic extract
  9. dry with materialwas dried over magnesium sulfate
  10. customevaporated to an oil
  11. distillationDistillation of the crude oil
  12. customgave 25.3 g

Sources & evidence

ORD record
ord-63fee64602b84290b7d828723dcc766a
Source dataset
uspto-grants-1990_05
Patent number
US04921994

Reaction notes

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