Perchloric Acid → HCID 21437941, compound

HRID 2397374Notes

Reaction equation

HRID 2397374 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=O)[CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:10][CH:9]=1.Cl(O)(=O)(=O)=O>C(O)(=O)C.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 24247Perchloric AcidHCID 21437988HCID 21437988, compound

Product 1

HCID 21437941HCID 21437941, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 17.8 gm (59 millimols) of methyl 4-(2'-chloro-4-biphenylyl)-4-oxo-butyrate in 150 ml of anhydrous acetic acid was admixed with 4 ml of perchloric acid of 70% and hydrogenated in the presence of 4 gm of palladium/barium sulfate (5%) at 5 atmospheres and at room temperature for 8 hours. The catalyst was vacuum-filtered off and the solvent was removed in vacuo; the residue was taken up in water and ethylene chloride. The carboxylic acid obtained from the separated organic phase was extracted with potassium carbonate and precipitated by acidifying. The free acid was extracted with ether, the ethereal solution was dried and distilled in a high vacuum (b.p. 186°-190° C. at 0.08 mm Hg). Yield: 62% of theory; m.p. 61.5°-63° C. (from cyclohexane/benzene). Melting point of the cyclohexylamine salt: 140° C. (from isopropanol).

Workup

  1. filtrationThe catalyst was vacuum-filtered off
  2. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-5a9bbe1b8fae46398ebd2932f2ed2be4
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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