Potassium Hydroxide → 6-Mercapto-8-methylthiooctanoic acid

HRID 247184Notes

Reaction equation

HRID 247184 reaction equation
C([O:3][C:4](=[S:17])[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]([S:13]C(=O)C)[CH2:10][CH2:11][CH3:12])C.[OH-].[K+]>CO.O>[SH:13][CH:9]([CH2:10][CH2:11][CH3:12])[CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:3])=[S:17]

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 53988615HCID 53988615, compound

Product 1

HCID 1784549696-Mercapto-8-methylthiooctanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

11.9 grams (40.7 mmoles) of 6-acetylthio-8-methylthiooctanoic acid ethyl ester (XI) were added to a solution of 7.5 grams (133.7 mmoles) of potassium hydroxide in 100 ml of methanol and 5 ml of water and the mixture heated at reflux for 10 hours under a cover of nitrogen. After a further 10 hours at room temperature the solvent was removed in a vacuum, the residue taken up on 100 ml of 3N hydrochloric acid and extracted three times, each time with 100 ml of ethyl acetate. After drying the combined extracts with magnesium sulfate the solvent was removed in a vacuum. The short path distillation of the residue gave 7.1 grams (78% of theory) of 6-mercapto-8-methylthiooctanoic acidas a pale yellow oil having a boiling point of 150° C. to 170° C. at 0.5 mbar.

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 10 hours under a cover of nitrogen
  3. customAfter a further 10 hours at room temperature the solvent was removed in a vacuum
  4. extractionextracted three times
  5. dry with materialAfter drying the combined extracts with magnesium sulfate the solvent
  6. customwas removed in a vacuum
  7. distillationThe short path distillation of the residue
  8. customgave 7.1 grams (78% of theory) of 6-mercapto-8-methylthiooctanoic acidas a pale yellow oil

Sources & evidence

ORD record
ord-ae6888ac8a8b40b78ba7df08fa4d9cd4
Source dataset
uspto-grants-1987_11
Patent number
US04705867

Reaction notes

Loading…