Phosphorus pentachloride → HCID 53754524, compound

HRID 2286792Notes

Reaction equation

HRID 2286792 reaction equation
P(Cl)(Cl)(Cl)(Cl)[Cl:2].[C:7]([CH2:15][CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1)=[O:18])(=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(Cl)(Cl)(Cl)Cl>[Cl:2][C:7]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[CH:15][CH2:16][C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:22]=1)=[O:18]

Participants

4

Reactant 2

HCID 24819Phosphorus pentachlorideHCID 23462498HCID 23462498, compound

Product 1

HCID 53754524HCID 53754524, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent2×

Procedure

To a refluxing mixture of phosphorus pentachloride (5.8 g) and carbon tetrachloride (25 ml) is slowly added m-phenoxybenzyl 3-benzoylpropionate (5 g) in carbon tetrachloride (10 ml) over about 45 minutes. Refluxing is continued about 0.5 hr and then the reaction is poured onto ice and extracted with ether. The ether extracts are combined, washed with saturated sodium bicarbonate, water and saturated sodium chloride, dried over calcium sulfate and solvent evaporated. The product is subjected to prep. TLC using 12% ethyl acetate/hexane and the major band collected to yield m-phenoxybenzyl 4-chloro-4-phenyl-3-butenoate.

Workup

  1. customover about 45 minutes
  2. temperatureRefluxing
  3. additionthe reaction is poured onto ice
  4. extractionextracted with ether
  5. washwashed with saturated sodium bicarbonate, water and saturated sodium chloride
  6. dry with materialdried over calcium sulfate and solvent
  7. customevaporated
  8. customthe major band collected

Sources & evidence

ORD record
ord-f51ca7e98cc3442f9e11ef025d8c955e
Source dataset
uspto-grants-1981_05
Patent number
US04267359

Reaction notes

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