Ammonium Chloride → HCID 21547160, compound

HRID 1605648Notes

Reaction equation

HRID 1605648 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]([CH:14]([CH3:18])[CH2:15][CH:16]=[O:17])=[CH:10][CH:9]=1.[CH3:19][Mg]Br.[Cl-].[NH4+]>CCOCC>[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]([CH:14]([CH3:18])[CH2:15][CH:16]([OH:17])[CH3:19])=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 21547137HCID 21547137, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 21547160HCID 21547160, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 96.9 gm (0.4 mol) of 3-(2'-fluoro-4-biphenylyl)-butanal (b.p. 112°-114°C at 0.04 mm Hg) in 200 ml of anhydrous ether was added dropwise to a stirred solution of 0.5 mol of methyl magnesium bromide in 200 ml of ether, and the resulting mixture was heated for two hours on a water bath, while stirring. Thereafter, the reaction mixture was cooled, then hydrolized by addition of 50 gm of crushed ice, and subsequently an aqueous 50% ammonium chloride solution was added until the initially formed precipitate dissolved again. The ethereal phase was separated, the aqueous phase was extracted twice with ether, the ethereal extracts were combined with the ether phase, thoroughly washed with water and dried over sodium sulfate, the ether was distilled off, and the residue was distilled in a high vacuum. 55.8 Gm (54% of theory) of a mixture of diastereoisomers of 4-(2'-fluoro-4-biphenylyl)-2-pentanol was obtained as a colorless oil having a boiling point of 122° -124°C at 0.06 mm Hg.

Workup

  1. temperaturethe resulting mixture was heated for two hours on a water bath
  2. temperatureThereafter, the reaction mixture was cooled
  3. dissolutiondissolved again
  4. customThe ethereal phase was separated
  5. extractionthe aqueous phase was extracted twice with ether
  6. washthoroughly washed with water
  7. dry with materialdried over sodium sulfate
  8. distillationthe ether was distilled off
  9. distillationthe residue was distilled in a high vacuum
  10. addition55.8 Gm (54% of theory) of a mixture of diastereoisomers of 4-(2'-fluoro-4-biphenylyl)-2-pentanol
  11. customwas obtained as a colorless oil

Sources & evidence

ORD record
ord-fa5c653ab29a45d9b111023716168bbe
Source dataset
uspto-grants-1976_04
Patent number
US03950427

Reaction notes

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