Potassium Hydroxide → HCID 22661465, compound

HRID 2270816Notes

Reaction equation

HRID 2270816 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][S:8][CH2:7][CH:6]2[C:11]([O:13]C)=[O:12])[O:4][CH2:3][CH2:2]1.[OH-].[K+]>C(O)C>[O:4]1[C:5]2([CH2:10][CH2:9][S:8][CH2:7][CH:6]2[C:11]([OH:13])=[O:12])[O:1][CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 85594397HCID 85594397, compound

Product 1

HCID 22661465HCID 22661465, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxylic acid, methyl ester (prepared according to Baldwin, J. J. et al. U.S. Pat. No. 4,803,286; 30.00 g, 0.137 mol) in ethanol (500 mL) and a solution of potassium hydroxide (16.80 g, 0.299 mol) in ethanol (300 mL) were combined and heated under reflux for 7 h. The solution was concentrated in vacuo and water was added. The mixture was extracted with ether, and the ether layer was discarded. The aqueous layer was made acidic and extracted with ether. The ether layers were washed, dried, and evaporated, and the residue was recrystallized from benzene/hexane to give 1,4-dioxa-8-thiaspiro[4.5]decane-6-carboxylic acid (17.8 g, 63%) as white crystals, mp 99-101° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 7 h
  3. concentrationThe solution was concentrated in vacuo and water
  4. additionwas added
  5. extractionThe mixture was extracted with ether
  6. extractionextracted with ether
  7. washThe ether layers were washed
  8. customdried
  9. customevaporated
  10. customthe residue was recrystallized from benzene/hexane

Sources & evidence

ORD record
ord-566bda5d35be4e468d6b306491d7dd0f
Source dataset
uspto-grants-2001_12
Patent number
US06331640B1

Reaction notes

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