Water → HCID 54188657, compound

HRID 258973Notes

Reaction equation

HRID 258973 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
20 °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 20 ml of absolute benzene whilst stirring at 20° 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-1b922dc6c3b64d5eaea1c107598994e3
Source dataset
uspto-grants-1977_07
Patent number
US04035413

Reaction notes

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