4-Hydroxybenzyl Alcohol → 125439-56-7

HRID 1741008Notes

Reaction equation

HRID 1741008 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][C:13]#[N:14].[C:15](=O)([O-])[O-].[K+].[K+].O>CC(=O)CC.[I-].[K+]>[C:13]([CH2:12][CH2:11][CH2:15][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][OH:7])=[CH:4][CH:3]=1)#[N:14]

Participants

7

Reactant 4

HCID 1254-Hydroxybenzyl AlcoholHCID 962WaterHCID 11430Potassium CarbonateHCID 170203-Bromopropionitrile

Product 1

HCID 14650338125439-56-7Yield 105.9%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 6569Methyl Ethyl KetoneSolvent

Procedure

The 4-hydroxybenzyl alcohol (24.8 g, 0.2 mol) and 3-bromopropionitrile (29.6 g, 0.2 mol) were dissolved in 250 ml of 2-butanone. Potassium carbonate (30 g) and catalytic potassium iodide (0.2 g) were added and the reaction was refluxed for 48 hrs. After cooling, water was added and the layers were separated. The organic layer was washed with water, 1N sodium hydroxide and water again, dried over MgSO4, filtered, and concentrated to dryness. The resultant oil was slurried in hexane and the precipitate was filtered to afford 40.5 g of the subtitle compound.

Workup

  1. temperaturethe reaction was refluxed for 48 hrs
  2. temperatureAfter cooling
  3. customthe layers were separated
  4. washThe organic layer was washed with water, 1N sodium hydroxide and water again
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-8bb10684f4dd4f538bf7ee59df7af6b5
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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