Hydrochloric Acid → 4-(4'-Fluoro-4-biphenylyl)-butyric acid

HRID 2397378Notes

Reaction equation

HRID 2397378 reaction equation
O.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16](=O)[CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=2)=[CH:6][CH:5]=1>[Zn].C1(C)C=CC=CC=1>[F:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 107308704-(4'-Fluoro-4-biphenylyl)-4-oxo-butyric acid

Product 1

HCID 108487954-(4'-Fluoro-4-biphenylyl)-butyric acidYield 79.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 1140TolueneSolvent

Procedure

15 ml of water, 35 ml of concentrated hydrochloric acid, 50 ml of toluene and 10 gm of 4-(4'-fluoro-4-biphenylyl)-4-oxo-butyric acid were added to 20 gm of amalgamated zinc (Org. Synthesis, Coll. Vol. III, 786), and the mixture was refluxed for 6 hours while stirring, another 10 ml of concentrated hydrochloric acid being added after 3 hours. Subsequently, the mixture was vacuum-filtered to remove the unreacted zinc, and the filtrate was extracted with ether. The residue remaining after evaporation of the ether was recrystallized from cyclohexane, yielding 7.5 gm (79% of theory) of colorless 4-(4'-fluoro-4-biphenylyl)-butyric acid, m.p. 118°-120° C.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. filtrationSubsequently, the mixture was vacuum-filtered
  3. customto remove the unreacted zinc
  4. extractionthe filtrate was extracted with ether
  5. customafter evaporation of the ether
  6. customwas recrystallized from cyclohexane

Sources & evidence

ORD record
ord-68b9ebb4cba44c47b410d2af416ee287
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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