Hydrochloric Acid → Cyclopentanesulfonic acid

HRID 486819Notes

Reaction equation

HRID 486819 reaction equation
[CH:1]1(S)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(OO)(=O)C.[S:12](=[O:15])([OH:14])[O-:13].[Na+].Cl>O.C(Cl)Cl>[CH:1]1([S:12]([OH:14])(=[O:13])=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Conditions

Temperature
15 °C

Procedure

A one liter three-neck flask was charged with 300 mL of methylene chloride and 25 grams (245 mmole) of cyclopentyl mercaptan to produce a reaction solution. The reaction solution was chilled to 15° C. in an ice-water bath and followed by the addition of 190 mL of 35% peroxy acetic acid. Said peroxy acetic acid was added over a period of about 3 hours and the reaction solution was maintained at a temperature of about 18°-26° C. After the reaction solution was stirred overnight at room temperature, 100 mL of water and 25 grams of sodium bisulfite were added followed by 2 additional hours of stirring. The reaction solution was then reduced on a rotovap and the pH was adjusted with dilute hydrochloric acid until a white solid precipitate formed. Said precipitate was isolated via filtration and dried in vacuo (50% yield of cyclopentane sulfonic acid).

Workup

  1. customto produce a reaction solution
  2. additionwas added over a period of about 3 hours
  3. temperaturethe reaction solution was maintained at a temperature of about 18°-26° C
  4. stirringof stirring
  5. customformed
  6. customwas isolated via filtration

Sources & evidence

ORD record
ord-55ee458409254b3b89790bdaa887300e
Source dataset
uspto-grants-1994_03
Patent number
US05292888

Reaction notes

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