Methanol → 6-Mercapto-8-methylthiooctanoic acid

HRID 1089401Notes

Reaction equation

HRID 1089401 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 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 53988615HCID 53988615, compound

Product 1

HCID 1784549696-Mercapto-8-methylthiooctanoic acidYield 84.5%

Reagents, catalysts & solvents 1

HCID 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 l00ml 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 in 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 acid as 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

Sources & evidence

ORD record
ord-ec376960acae4e2b94a4d1ff934e5a00
Source dataset
uspto-grants-1990_10
Patent number
US04966732

Reaction notes

Loading…