Phosphoric Acid → HCID 23005248, compound

HRID 2397368Notes

Reaction equation

HRID 2397368 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.P(=O)(O)(O)O.[H][H]>C(O)(=O)C.C(OCC)(=O)C.[Pd]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 1004Phosphoric AcidHCID 14116665HCID 14116665, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23005248HCID 23005248, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 12.3 gm (42.7 millimols) of 4-(4'-chloro-4-biphenylyl)-4-oxo-butyric acid in 150 ml of acetic acid was admixed with 4 ml of orthophosphoric acid of 89% and hydrogenated in the presence of 4 gm of palladium/barium sulfate (5%) at a hydrogen pressure of 5 atmospheres and at room temperature. The catalyst was vacuum-filtered off, and the solvent was evaporated. The residue was dissolved in ether, the organic phase was washed with water and evaporated to dryness. The free acid thus obtained was dissolved again in ethyl acetate, the solution was filtered and mixed with a small excess of cyclohexylamine. Yield: 9.5 gm (62.5% of theory); m.p. 187°-190° C. (cyclohexylamine salt). Melting point of the free acid: 136°-137° C.

Workup

  1. filtrationThe catalyst was vacuum-filtered off
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in ether
  4. washthe organic phase was washed with water
  5. customevaporated to dryness
  6. customThe free acid thus obtained
  7. filtrationthe solution was filtered
  8. additionmixed with a small excess of cyclohexylamine
  9. custom136°-137° C.

Sources & evidence

ORD record
ord-40499d4a897e4be69604be5d5cc1e75e
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

Loading…