Phosphorus oxide (P4O10) → Ethyl 4-(m-benzoylphenyl)-3-butenoate

HRID 1579776Notes

Reaction equation

HRID 1579776 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[C:15]([C:23]1[CH:24]=[C:25]([CH2:29][CH:30](O)[CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:26]=[CH:27][CH:28]=1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C(C)=CC=CC=1>[C:15]([C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH2:31][C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH:26]=[CH:27][CH:28]=1)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 14812Phosphorus oxide (P4O10)HCID 21495623Ethyl 4-(m-benzoyl-phenyl)-3-hydroxybutyrate

Product 1

HCID 53820247Ethyl 4-(m-benzoylphenyl)-3-butenoate

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

315 mg of phosphoric anhydride were added to a solution of 1.12 g of ethyl 4-(m-benzoyl-phenyl)-3-hydroxy-butyrate in 20 ml of xylene and the mixture was refluxed for 2 hours and then cooled to room temperature. The organic phase was washed with water, then with an aqueous saturated sodium bicarbonate solution and then water, dried over sodium sulfate, treated with activated carbon, filtered and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with methylene chloride which was evaporated to dryness to obtain ethyl 4-(m-benzoyl-phenyl)-3-butenoate whose ultraviolet spectrum was in accord with the structure.

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. washThe organic phase was washed with water
  3. dry with materialwith an aqueous saturated sodium bicarbonate solution and then water, dried over sodium sulfate
  4. additiontreated with activated carbon
  5. filtrationfiltered
  6. customevaporated to dryness under reduced pressure
  7. customThe residue was chromatographed over silica gel
  8. washwas eluted with methylene chloride which
  9. customwas evaporated to dryness

Sources & evidence

ORD record
ord-7c44246a6be14a178d36132030392247
Source dataset
uspto-grants-1976_01
Patent number
US03931302

Reaction notes

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