Potassium Hydroxide → HCID 11601613, compound

HRID 1953429Notes

Reaction equation

HRID 1953429 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2([C:17]([O:19]CC)=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+]>C(O)C>[C:1]1([S:7]([CH2:10][C:11]2([C:17]([OH:19])=[O:18])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 23297890HCID 23297890, compound

Product 1

HCID 11601613HCID 11601613, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Further, 1.43 g (4.6 mmol) of the ethyl 1-phenylsulfonylmethylcyclohexanecarboxylate and 1.52 g (23.0 mmol) of potassium hydroxide were dissolved in aqueous solution of 90% ethanol. After heating reflux for 18 hours, the reaction mixture was concentrated under reduced pressure. The obtained residue was dissolved in water and washed with ether. The resulting water layer was made acid (pH=2) by the addition of 4N-hydrochloric acid thereto and then extracted with ethyl acetate and washed with 1N-hydrochloric acid and saturated brine. The obtained organic layer was dried over anhyrous sodiumsulfate and concentrated under reduced pressure, whereby 1.22 g of the captioned 1-phenylsulfonylmethylcyclohexane-carboxylic acid was obtained in a yield of 60%.

Workup

  1. temperatureAfter heating
  2. temperaturereflux for 18 hours
  3. concentrationthe reaction mixture was concentrated under reduced pressure
  4. dissolutionThe obtained residue was dissolved in water
  5. washwashed with ether
  6. additionby the addition of 4N-hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. washwashed with 1N-hydrochloric acid and saturated brine
  9. dry with materialThe obtained organic layer was dried over anhyrous sodiumsulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2252a8b24b1c44e18784f52d0060ea26
Source dataset
uspto-grants-2000_09
Patent number
US06117870

Reaction notes

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