Sodium Acetate → 2-[4-(Hydroxymethyl)phenyl]benzonitrile

HRID 1609173Notes

Reaction equation

HRID 1609173 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]#[N:16])=[CH:5][CH:4]=1.C([O-])(=[O:19])C.[Na+]>C(O)(=O)C>[C:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][OH:19])=[CH:4][CH:5]=1)#[N:16]

Participants

4

Reactant 2

HCID 517045Sodium AcetateHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

Product 1

HCID 13938962-[4-(Hydroxymethyl)phenyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

250 g of 4-bromomethyl-2'-cyano-biphenyl, 150 g of sodium acetate and 2.5 1 of glacial acetic acid are heated to reflux overnight. The mixture is then concentrated in a high vacuum, and the residue is taken up in ethyl acetate. This ethyl acetate mixture is extracted in succession with water, sodium hydrogencarbonate solution and brine and then evaporated on a rotary evaporator. The crude product is dissolved in 3.1 l of ethanol, the solution is treated with 430 ml of 2N NaOH, the mixture is stirred overnight at room temperature and then concentrated, and the residue is taken up in ethyl acetate. The mixture is washed in succession with water and sodium carbonate solution and concentrated. The residue is suspended in hexane, the suspension is filtered with suction, and the filter cake is washed and dried at 60° in a high vacuum for 20 hours. 2'-Cyano-4-hydroxymethyl-biphenyl is thus obtained in the form of a white powder [1H-NMR (DMSO-d6): 4.58 ppm (d, 2H); 5.3 ppm (t, 1H); 7.6 to 8.0 ppm (m, 8H)].

Workup

  1. temperatureto reflux overnight
  2. concentrationThe mixture is then concentrated in a high vacuum
  3. extractionThis ethyl acetate mixture is extracted in succession with water, sodium hydrogencarbonate solution and brine
  4. customevaporated on a rotary evaporator
  5. dissolutionThe crude product is dissolved in 3.1 l of ethanol
  6. additionthe solution is treated with 430 ml of 2N NaOH
  7. concentrationconcentrated
  8. washThe mixture is washed in succession with water and sodium carbonate solution
  9. concentrationconcentrated
  10. filtrationthe suspension is filtered with suction
  11. washthe filter cake is washed
  12. customdried at 60° in a high vacuum for 20 hours

Sources & evidence

ORD record
ord-3d808cba34c3476e8642cd5d275c9ac3
Source dataset
uspto-grants-1995_03
Patent number
US05399578

Reaction notes

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