Ethanethiol → Ethyl 1-methylcyclopropanecarboxylate

HRID 1380531Notes

Reaction equation

HRID 1380531 reaction equation
[CH3:1][C:2]1([C:5]([OH:7])=[O:6])[CH2:4][CH2:3]1.S(Cl)(Cl)=O.[CH2:12](S)[CH3:13]>C(OCC)C>[CH2:12]([O:6][C:5]([C:2]1([CH3:1])[CH2:4][CH2:3]1)=[O:7])[CH3:13]

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 24386Thionyl ChlorideHCID 813261-Methylcyclopropanecarboxylic acid

Product 1

HCID 544234Ethyl 1-methylcyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

100 g of 1-methylcyclopropanoic acid was added to 150 ml of diethyl ether. The system was cooled to 0°-5° C. and 119 gm of thionyl chloride was added dropwise over a period of time. After addition, the system was heated at reflux for 8 hours. The system was then cooled to 0°-5° C. and 62 gm of ethanethiol was added dropwise. The system was heated at reflux for 6 hours and then stirred at room temperature for 72 hours. The diethyl ether was removed by stripping to give the 1-methylcyclopropanoic acid ethyl ester.

Workup

  1. temperatureThe system was cooled to 0°-5° C.
  2. additionAfter addition
  3. temperaturethe system was heated
  4. temperatureat reflux for 8 hours
  5. temperatureThe system was then cooled to 0°-5° C.
  6. temperatureThe system was heated
  7. temperatureat reflux for 6 hours
  8. customThe diethyl ether was removed

Sources & evidence

ORD record
ord-44bed3a7958c4b10b0c92577dbf789f4
Source dataset
uspto-grants-1986_04
Patent number
US04582828

Reaction notes

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