Hydrochloric Acid → 3-(2-Fluoro-4-biphenylyl)-1-butanol

HRID 918151Notes

Reaction equation

HRID 918151 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:13])[CH2:9][C:10](O)=[O:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.Cl>O1CCCC1.O>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:13])[CH2:9][CH2:10][OH:11])[CH:5]=[CH:4][C:3]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 215232673-(3-Fluoro-4-phenylphenyl)butanoic acid

Product 1

HCID 215232653-(2-Fluoro-4-biphenylyl)-1-butanol

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 25.83 gm (0.10 mol) of 3-(2-fluoro-4-biphenylyl)-butyric acid in 100 ml of absolute tertrahydrofuran was added dropwise at room temperature to a stirred suspension of 2.85 gm (0.075 mol) of lithium aluminum hydride in 100 ml of absolute tetrahydrofuran, the resulting mixture was stirred for 60 minutes more at room temperature and for 30 minutes at 30°-35°C, and then ethyl acetate was added dropwise until no more exothermic reaction occurred. The reaction mixture was then stirred for 15 minutes at room temperature, and thereafter first 50 ml of water and then aqueous 5% hydrochloric acid were added dropwise, accompanied by exterior cooling with ice water, until the precipitate first formed dissolved. The solution was stirred into 2 liters of water, extracted exhaustively with ether, and the combined ether extracts were washed successively with water, saturated aqueous sodium bicarbonate solution and again with water, dried over sodium sulfate, filtered, and evaporated. 18.0 gm (74% of theory) of colorless 3-(2-fluoro-4-biphenylyl)-1-butanol of the formula ##EQU25## which had a melting point of 72°C after recrystallization from cyclohexane.

Workup

  1. stirringThe reaction mixture was then stirred for 15 minutes at room temperature
  2. customfirst formed
  3. dissolutiondissolved
  4. extractionextracted exhaustively with ether
  5. washthe combined ether extracts were washed successively with water, saturated aqueous sodium bicarbonate solution and again with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customafter recrystallization from cyclohexane

Sources & evidence

ORD record
ord-a742ebdeebee401bb76ba234c1808f8d
Source dataset
uspto-grants-1976_07
Patent number
US03969419

Reaction notes

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