Thionyl Chloride → Ethyl (2-chloro-6-oxocyclohex-1-en-1-yl)acetate

HRID 2292153Notes

Reaction equation

HRID 2292153 reaction equation
O.[O:2]=[C:3]1[CH2:8][CH2:7][CH2:6][C:5](=O)[CH:4]1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12].S(Cl)([Cl:18])=O>C(Cl)Cl>[Cl:18][C:5]1[CH2:6][CH2:7][CH2:8][C:3](=[O:2])[C:4]=1[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 12355684HCID 12355684, compound

Product 1

HCID 14330442Ethyl (2-chloro-6-oxocyclohex-1-en-1-yl)acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A slurry of ethyl α-(2,6-dioxocyclohexyl)acetate hydrate (1.53 kg) in methylene chloride (7.7L) is brought to reflux and then thionyl chloride (1.80 kg) is added dropwise over a period of 1.75 hours. The solution is refluxed for 3 hours and then evaporated in vacuo to yield an oil which is distilled to give ethyl α-(2-chloro-6-oxocyclohex-1-enyl)acetate as a yellow oil, bp 115°-125°/0.2 mm.

Workup

  1. temperatureto reflux
  2. temperatureThe solution is refluxed for 3 hours
  3. customevaporated in vacuo
  4. customto yield an oil which
  5. distillationis distilled

Sources & evidence

ORD record
ord-852f04908fb64e259b45c1c4b91b9d43
Source dataset
uspto-grants-1989_01
Patent number
US04801605

Reaction notes

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