Pyridine → 6-Chloro-8-methylthiooctanoic acid ethyl ester

HRID 247180Notes

Reaction equation

HRID 247180 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:7][C:8](=[S:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13](O)[CH2:14][CH2:15][CH3:16])[CH3:6].N1C=CC=CC=1>ClCCl>[CH2:5]([O:7][C:8](=[S:18])[CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([Cl:3])[CH2:14][CH2:15][CH3:16])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 545259706-Hydroxy-8-methylthiooctanoic acid ethyl ester

Product 1

HCID 536593926-Chloro-8-methylthiooctanoic acid ethyl esterYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

89.25 grams (0.7 mole) of thionyl chloride at +5° C. were slowly dropped into a solution of 137.0 grams (0.59 mole) of 6-hydroxy-8-methylthiooctanoic acid ethyl ester (VIb) and 1 ml of pyridine in 300 ml of dichloromethane. After stirring for 1 hour at +10° C. the mixture was heated for 3 hours at reflux and subsequently concentrated in a vacuum. The residue was treated with 200 ml of water and extracted with dichloromethane. After drying the combined extracts with sodium sulfate the solvent was removed in a vacuum. By fractional distillation there were obtained 125.1 grams (84% of theory) of 6-chloro-8-methylthiooctanoic acid ethyl ester as a colorless oil having a boiling point of 135° C. to 145° C. at 1 mbar.

Workup

  1. temperaturewas heated for 3 hours
  2. temperatureat reflux
  3. concentrationsubsequently concentrated in a vacuum
  4. additionThe residue was treated with 200 ml of water
  5. extractionextracted with dichloromethane
  6. dry with materialAfter drying the combined extracts with sodium sulfate the solvent
  7. customwas removed in a vacuum
  8. distillationBy fractional distillation there

Sources & evidence

ORD record
ord-46bb3864cde948f0a53326263fda093b
Source dataset
uspto-grants-1987_11
Patent number
US04705867

Reaction notes

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