Potassium Hydroxide → 4-[2-(Ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxylic acid

HRID 605508Notes

Reaction equation

HRID 605508 reaction equation
[CH2:1]([S:3]([CH2:6][CH2:7][C:8]12[CH2:15][CH2:14][C:11]([C:16]([O:18]C)=[O:17])([CH2:12][CH2:13]1)[CH2:10][CH2:9]2)(=[O:5])=[O:4])[CH3:2].[OH-].[K+]>O.CO>[CH2:1]([S:3]([CH2:6][CH2:7][C:8]12[CH2:13][CH2:12][C:11]([C:16]([OH:18])=[O:17])([CH2:14][CH2:15]1)[CH2:10][CH2:9]2)(=[O:5])=[O:4])[CH3:2]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 22591696Methyl 4-[2-(ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxylate

Product 1

HCID 225917104-[2-(Ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxylic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
60 °C

Procedure

Ester 1-3 (880 mg, 3 mmol) was dissolved in 10% water/methanol solution (100 mL) and treated with 1 g of potassium hydroxide. The reaction was heated at 60° C. for 1 h then at 45° C. overnight. The mixture was concentrated in vacuo then acidified to pH 2 with 1M HCl and extracted with three portions of methylene chloride. The organic layers were combined, dried over anhydrous sodium sulfate and evaporated to give 4-[2-(ethylsulfonyl)ethyl]bicyclo[2.2.2]octane-1-carboxylic acid (1-4) (810 mg).

Workup

  1. customat 45° C.
  2. customovernight
  3. concentrationThe mixture was concentrated in vacuo
  4. extractionextracted with three portions of methylene chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-f5b42696ee1a4a73b0dc09cf057d1720
Source dataset
uspto-grants-2011_03
Patent number
US07915252B2

Reaction notes

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