Thionyl Chloride → Ethyl 8-(2-chloroethylthio)-12-acetoxyheptadecanoate

HRID 1833453Notes

Reaction equation

HRID 1833453 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][S:8][CH:9]([CH2:21][CH2:22][CH2:23][CH:24]([O:30][C:31](=[O:33])[CH3:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>C1C=CC=CC=1>[Cl:3][CH2:6][CH2:7][S:8][CH:9]([CH2:21][CH2:22][CH2:23][CH:24]([O:30][C:31](=[O:33])[CH3:32])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21317600HCID 21317600, compound

Product 1

HCID 21317532Ethyl 8-(2-chloroethylthio)-12-acetoxyheptadecanoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Thionyl chloride (13.1 g., 0.11 mole) is added dropwise with stirring to a solution of ethyl 8-(2-hydroxyethylthio)-12 -acetoxyheptadecanoate (43.2 g., 0.10 mole) in benzene (150 ml.). The solution is heated at reflux for 2 hours. Then, the solvent and excess thionyl chloride are removed by evaporation in vacuo to leave the title compound as an orange yellow residual oil.

Workup

  1. temperatureThe solution is heated
  2. temperatureat reflux for 2 hours
  3. customThen, the solvent and excess thionyl chloride are removed by evaporation in vacuo

Sources & evidence

ORD record
ord-83aeadf1aed448cda60418b5030e5abd
Source dataset
uspto-grants-1978_01
Patent number
US04066675

Reaction notes

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