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

HRID 2083286Notes

Reaction equation

HRID 2083286 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-53f8f293b04e41bdbdd36b7672820038
Source dataset
uspto-grants-1978_04
Patent number
US04085125

Reaction notes

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