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

HRID 1739065Notes

Reaction equation

HRID 1739065 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>[OH:19][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

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'-cyanobiphenyl (EP 253,310), 150 g of sodium acetate and 2.5 litres of glacial acetic acid are heated to reflux overnight and the mixture is then concentrated in a high vacuum. The residue is taken up in ethyl acetate, extracted with water, sodium bicarbonate and brine and the solvent is evaporated on a rotary evaporator. The crude product is dissolved in 3.1 litres of ethanol, treated with 430 ml of 2N NaOH and stirred overnight at room temperature. The reaction mixture is concentrated, taken up in ethyl acetate, washed with water and sodium carbonate and concentrated. The residue is suspended in hexane, filtered off with suction, washed and dried at 60° in a high vacuum for 20 hours. 4-Hydroxymethyl-2'-cyanobiphenyl is obtained as a white powder. 1H-NMR (DMSO): 4.58 ppm (d, 2 H), 5.3 ppm (t, 1 H), 7.6-8 ppm (aromatics, 8 H).

Workup

  1. temperatureto reflux overnight
  2. concentrationthe mixture is then concentrated in a high vacuum
  3. extractionextracted with water, sodium bicarbonate and brine
  4. customthe solvent is evaporated on a rotary evaporator
  5. dissolutionThe crude product is dissolved in 3.1 litres of ethanol
  6. additiontreated with 430 ml of 2N NaOH
  7. concentrationThe reaction mixture is concentrated
  8. washwashed with water and sodium carbonate
  9. concentrationconcentrated
  10. filtrationfiltered off with suction
  11. washwashed
  12. customdried at 60° in a high vacuum for 20 hours

Sources & evidence

ORD record
ord-1006aa69b3fd40258350f37dada293a8
Source dataset
uspto-grants-1999_10
Patent number
US05965592

Reaction notes

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