Thionyl Chloride → Ethyl 12-(acetyloxy)-8-(chlorocarbonyl)heptadecanoate

HRID 372884Notes

Reaction equation

HRID 372884 reaction equation
[C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(O)=[O:2].S(Cl)([Cl:31])=O>C1C=CC=CC=1>[Cl:31][C:1]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21317594HCID 21317594, compound

Product 1

HCID 20322197Ethyl 12-(acetyloxy)-8-(chlorocarbonyl)heptadecanoate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of ethyl 8-carboxy-12-acetoxyheptadecanoate (12.0 g., 0.03 mole) and thionyl chloride (7.2 g., 0.06 mole) in benzene (50 ml.) is refluxed for 2.5 hours. Volatile materials are removed by using a rotary evaporator in vacuo. The residual product, ethyl 8-chlorocarbonyl-12-acetoxyheptadecanoate, is a viscous liquid weighing 12.5 g. (100%), ir (neat) 1790 cm-1 (acid chloride C=O), 1730 cm-1 (ester C=O). This material is used directly in the next step.

Workup

  1. customVolatile materials are removed
  2. customa rotary evaporator in vacuo

Sources & evidence

ORD record
ord-9cdc6015d4494230a398db198c9c9195
Source dataset
uspto-grants-1978_05
Patent number
US04092356

Reaction notes

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