Hydrogen iodide → 4-(4'-Fluoro-4-biphenylyl)-butyric acid

HRID 2397380Notes

Reaction equation

HRID 2397380 reaction equation
[Na].[F:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15](O)[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.I.S(=O)(O)[O-].[Na+]>C(O)(=O)C.O>[F:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[CH:11][CH:10]=2)=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 24841Hydrogen iodideHCID 5360545SodiumHCID 214379434-(4'-Fluoro-4-biphenylyl)-4-hydroxy-butyric acidHCID 23665763Sodium Bisulfite

Product 1

HCID 108487954-(4'-Fluoro-4-biphenylyl)-butyric acid

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

1.50 gm (0.005 mol) of the sodium salt of 4-(4'-fluoro-4-biphenylyl)-4-hydroxy-butyric acid were refluxed in 15 ml of glacial acetic acid and 25 ml of hydroiodic acid (d=2.00) for 10 hours, and then the reaction mixture was poured into a solution of 5 gm of sodium bisulfite in 400 ml of water. The colorless precipitate was collected and recrystallized from cyclohexane, yielding 4-(4'-fluoro-4-biphenylyl)-butyric acid, m.p. 119°-120° C. Melting point of the cyclohexylamine salt: 177° C. (precipitated from ethyl acetate). Yield: 1.3 gm.

Workup

  1. customThe colorless precipitate was collected
  2. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-68dbfcc8ca774bf0b0f0fee5086db8c6
Source dataset
uspto-grants-1977_05
Patent number
US04021479

Reaction notes

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