3-Hydroxybenzyl alcohol → 2-[3-(Hydroxymethyl)phenoxy]acetonitrile

HRID 585500Notes

Reaction equation

HRID 585500 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH2:5][OH:6].CC(C)=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]#[N:23]>CN(C)C=O.C1(C)C=CC=CC=1.C(OCC)(=O)C>[OH:6][CH2:5][C:4]1[CH:3]=[C:2]([CH:9]=[CH:8][CH:7]=1)[O:1][CH2:21][C:22]#[N:23]

Participants

7

Reactant 4

HCID 1023-Hydroxybenzyl alcoholHCID 180AcetoneHCID 11430Potassium CarbonateHCID 11534Bromoacetonitrile

Product 1

HCID 113211372-[3-(Hydroxymethyl)phenoxy]acetonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21584019Toluene ethylacetateSolvent

Procedure

25.3 g (203.8 mmol) of 3-hydroxybenzyl alcohol are dissolved in 50 ml of dimethylformamide, and 400 ml of acetone and 28.17 g (203.8 mmol) of finely ground potassium carbonate are added. After 5 minutes of stirring, 24.45 g (203.8 mmol) of bromoacetonitrile are added, and the mixture is boiled under reflux for 72 hours. The mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is dissolved in ethyl acetate and washed with 10% strength aqueous sodium hydroxide solution and then with water. The organic phase is dried over magnesium sulfate and filtered through a short silica gel column (mobile phase toluene->toluene/ethyl acetate=1:1). Evaporation gives 163.18 g (86% of theory) of an oil. Rf (SiO2, toluene/ethyl acetate=1:1)=0.41.

Workup

  1. temperatureunder reflux for 72 hours
  2. filtrationThe mixture is filtered
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with 10% strength aqueous sodium hydroxide solution
  6. dry with materialThe organic phase is dried over magnesium sulfate
  7. filtrationfiltered through a short silica gel column (mobile phase toluene->toluene/ethyl acetate=1:1)
  8. customEvaporation
  9. customgives 163.18 g (86% of theory) of an oil

Sources & evidence

ORD record
ord-18095aabfc5e4093951271d33504df9b
Source dataset
uspto-grants-2005_08
Patent number
US06933295B2

Reaction notes

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