Water → HCID 19036864, compound

HRID 2397381Notes

Reaction equation

HRID 2397381 reaction equation
[F: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)/[CH:15]=[CH:16]/[C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1.I.O.S(=O)(O)[O-].[Na+]>C(O)(=O)C>[F: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

6

Reactant 4

HCID 962WaterHCID 24841Hydrogen iodideHCID 21437942HCID 21437942, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 19036864HCID 19036864, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.10 gm (0.004 mol) of 4-(2'-fluoro-4-biphenylyl)-4-oxo-crotonic acid were refluxed while stirring, in 10 ml of glacial acetic acid and 20 ml hydroiodic acid (d=2.00) for 12 hours. Subsequently, the solution was poured into 200 ml of water, the aqueous mixture was decolorized with sodium bisulfite, and extracted twice with 100 ml of ether each. The ether solution was washed with water and evaporated; the solid residue was refluxed with 150 ml of cyclohexane, the undissolved starting material was vacuum-filtered off, and the cyclohexane solution was evaporated to dryness. The residue was dissolved in 20 ml of ethyl acetate, and by addition of cyclohexylamine the cyclohexylamine salt of 4-(2'-fluoro-4-biphenylyl)-butyric acid was precipitated; m.p. 132°-134° C., after recrystallization from ethyl acetate/ethanol. Yield: 0.60 gm.

Workup

  1. extractionextracted twice with 100 ml of ether each
  2. washThe ether solution was washed with water
  3. customevaporated
  4. temperaturethe solid residue was refluxed with 150 ml of cyclohexane
  5. filtrationwas vacuum-filtered off
  6. customthe cyclohexane solution was evaporated to dryness
  7. dissolutionThe residue was dissolved in 20 ml of ethyl acetate
  8. additionby addition of cyclohexylamine the cyclohexylamine salt of 4-(2'-fluoro-4-biphenylyl)-butyric acid
  9. customwas precipitated
  10. customm.p. 132°-134° C., after recrystallization from ethyl acetate/ethanol

Sources & evidence

ORD record
ord-1816188c6ca742878555e5ee886f97bc
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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