Water → HCID 54188657, compound

HRID 1974229Notes

Reaction equation

HRID 1974229 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[CH2:7]([O:9][C:10](=[O:17])[CH2:11][C:12](=O)[CH2:13][CH2:14][CH3:15])[CH3:8].O>C1C=CC=CC=1>[CH2:7]([O:9][C:10](=[O:17])[CH:11]=[C:12]([Cl:2])[CH2:13][CH2:14][CH3:15])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 24819Phosphorus pentachlorideHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 54188657HCID 54188657, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
0 °C

Procedure

280 g of phosphorus pentachloride are added in portions over the course of 2 hours to a solution of 200 g of 3-oxo-hexanoic acid ethyl ester in 200 ml of absolute benzene whilst stirring at 0° C. 200 ml of water are then added dropwise with intense cooling so that the temperature never rises above 0° C. The mixture is stirred for a further 12 hours at 0° C. The organic phase is then separated off, washed with twice 100 ml of ice-cold 2 N sodium hydroxide solution and with twice 100 ml of water, dried over sodium sulphate and evaporated in vacuo. Fractional distillation of the evaporation residue gives, in the fraction boiling at 98°-102° C (20 mm), crude 3-chloro-2-hexenoic acid ethyl ester, which is used direct for further conversion.

Workup

  1. temperaturewith intense cooling so that the temperature never rises above 0° C
  2. stirringThe mixture is stirred for a further 12 hours at 0° C
  3. customThe organic phase is then separated off
  4. washwashed with twice 100 ml of ice-cold 2 N sodium hydroxide solution and with twice 100 ml of water
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. distillationFractional distillation of the evaporation residue

Sources & evidence

ORD record
ord-23caced0cbcd492c82a2f9fd1fd753e4
Source dataset
uspto-grants-1976_12
Patent number
US04000183

Reaction notes

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