Hydrochloric Acid → HCID 178443546, compound

HRID 1089398Notes

Reaction equation

HRID 1089398 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Na].C([O:12][C:13](=[S:23])[CH2:14][CH2:15][CH2:16][CH2:17][CH:18](Cl)[CH2:19][CH2:20][CH3:21])C.[OH-].[K+].Cl>O>[CH2:1]([S:8][CH:18]([CH2:19][CH2:20][CH3:21])[CH2:17][CH2:16][CH2:15][CH2:14][C:13]([OH:12])=[S:23])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 7509Benzyl mercaptanHCID 14797Potassium HydroxideHCID 5360545SodiumHCID 536593926-Chloro-8-methylthiooctanoic acid ethyl ester

Product 1

HCID 178443546HCID 178443546, compoundYield 104.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

12.4 grams (0.1 mole) of benzyl mercaptan were added to a solution of 2.3 grams of sodium in 75 ml of water free ethanol (corresponding to 0.1 mole of sodium ethanolate) and the mixture stirred for 0.5 hour at +10° C. Thereupon there were added 22.72 grams (0.09 mole) of 6-chloro-8-methylthiooctanoic acid ethyl ester (X) and the mixture heated for 20 hours at reflux. To the cooled reaction mixture there were added 11.2 grams (0.17 mole) of potassium hydroxide and stirring was carried out for 20 hours at room temperature. After addition of 500 ml of water the mixture was acidified with dilute hydrochloric acid, extracted with dichloromethane, the combined extracts washed with saturated aqueous sodium chloride solution and dried with sodium sulfate. By distilling off the solvent in a vacuum there were obtained 28.0 grams (96% of theory) of crude 6-benzylthio-8-methylthiooctanoic acid.

Workup

  1. temperaturethe mixture heated for 20 hours
  2. temperatureat reflux
  3. customTo the cooled reaction mixture there
  4. stirringstirring
  5. waitwas carried out for 20 hours at room temperature
  6. extractionextracted with dichloromethane
  7. washthe combined extracts washed with saturated aqueous sodium chloride solution
  8. dry with materialdried with sodium sulfate
  9. distillationBy distilling off the solvent in a vacuum there

Sources & evidence

ORD record
ord-d5113101b31f45a8836068f3cd75bb7f
Source dataset
uspto-grants-1990_10
Patent number
US04966732

Reaction notes

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