Hydrochloric Acid → HCID 54550783, compound

HRID 2107927Notes

Reaction equation

HRID 2107927 reaction equation
P(Cl)(Cl)(Cl)(Cl)Cl.[CH3:7][C:8]1[CH:21]=[CH:20][C:11]([C:12]([CH2:14][C:15](OCC)=[O:16])=O)=[CH:10][CH:9]=1.P(Cl)(Cl)[Cl:23].[ClH:26]>>[Cl:26][C:12]([C:11]1[CH:20]=[CH:21][C:8]([CH3:7])=[CH:9][CH:10]=1)=[CH:14][C:15]([Cl:23])=[O:16]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 24387Phosphorus trichlorideHCID 24819Phosphorus pentachloride2×HCID 292637Ethyl 3-(4-methylphenyl)-3-oxopropanoate

Product 1

HCID 54550783HCID 54550783, compound

Procedure

A one liter flask was fitted with a mechanical stirrer, CaCl2 drying tube, condenser and a sidearm addition funnel. 100 gms of PCl5 was placed in the flask. 39 gms of ethyl 4-methylbenzoylacetate and 100 gms of PCl3 were mixed and slowly added to the PCl5 at room temperature. The reaction mixture evolved HCl. After 30 minutes the mixture was cautiously refluxed for 2 hours. At this time PCl3 and POCl3 were distilled from the reaction mixture at reduced pressure. The residue was then distilled at 0.5 mm (bp=116°-121°) to provide 32 gms of β-chloro-4-methylcinnamoyl chloride as a clear oil.

Workup

  1. customA one liter flask was fitted with a mechanical stirrer, CaCl2 drying tube, condenser and a sidearm addition funnel
  2. temperatureAfter 30 minutes the mixture was cautiously refluxed for 2 hours
  3. distillationAt this time PCl3 and POCl3 were distilled from the reaction mixture at reduced pressure
  4. distillationThe residue was then distilled at 0.5 mm (bp=116°-121°)

Sources & evidence

ORD record
ord-f8b36d575d5340ec84ea93d24765add3
Source dataset
uspto-grants-1990_06
Patent number
US04936904

Reaction notes

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