Hydrochloric Acid → 4'-(1-Hydroxyethyl)biphenyl-2-carbonitrile

HRID 2062735Notes

Reaction equation

HRID 2062735 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][CH:4]=1)=[O:2].[CH3:17][Mg]Br.Cl>O1CCCC1>[OH:2][CH:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:10]([C:15]#[N:16])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:7][CH:8]=1)[CH3:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 13940624'-Formyl-[1,1'-biphenyl]-2-carbonitrileHCID 178418573HCID 178418573, compound

Product 1

HCID 670083834'-(1-Hydroxyethyl)biphenyl-2-carbonitrileYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4′-formylbiphenyl-2-carbonitrile (10.00 g) in tetrahydrofuran (100 mL) was slowly added dropwise a 1 M solution (50 mL) of methylmagnesium bromide in tetrahydrofuran at 0° C., and the mixture was stirred at room temperature for 2 hr. The reaction mixture was poured into 1 M hydrochloric acid (60 mL), and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography to give the title compound as a pale-yellow oil (10.03 g, 93%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-458db507fa484d65946a38ce32a31a68
Source dataset
uspto-grants-2012_10
Patent number
US08283353B2

Reaction notes

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