4-Hydroxybenzaldehyde → HCID 12419541, compound

HRID 1634120Notes

Reaction equation

HRID 1634120 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.CC[O-].[Na+].Br[CH2:15][CH2:16][CH2:17][C:18]#[N:19]>CCO>[C:18]([CH2:17][CH2:16][CH2:15][O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)#[N:19]

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 214124-BromobutyronitrileHCID 2723922Sodium ethoxide

Product 1

HCID 12419541HCID 12419541, compoundYield 126.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
90 °C

Procedure

4-Hydroxybenzaldehyde (20 mmol) was dissolved in absolute EtOH (150 mL) and treated with solid NaOEt (24 mmol). After stirring for 15 minutes, 4-bromobutyronitrile (24 mmol) was added and reaction mixture was heated overnight at 90° C. in an oil bath. After letting the reaction cool to room temperature, volatiles were removed, the residue was taken up in ice, adjusted to pH 6 with 1N sulfuric acid, and extracted with methylene chloride. The organic phase was washed with brine, dried over MgSO4 and concentrated. Chromatography over silica gel (eluant, 5% EtOAc in hexanes) gave the 4-(3-cyanopropoxy)benzaldehyde (4.8 g, 58%).

Workup

  1. customreaction mixture
  2. temperaturecool to room temperature
  3. customvolatiles were removed
  4. extractionextracted with methylene chloride
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-37895a13fd5144e387b90ba9c93d9f97
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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