Hydrochloric Acid → 2-Formyl-2-phenylacetonitrile

HRID 1690851Notes

Reaction equation

HRID 1690851 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:10](OCC)=[O:11].[H-].[Na+].Cl>O1CCCC1>[O:11]=[CH:10][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:8]#[N:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8025Ethyl formateHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

Product 1

HCID 3458802-Formyl-2-phenylacetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

3-Oxo-2-phenylpropanenitrile was prepared by addition of a mixture of phenylacetonitrile (0.90 g, 7.68 mmol) and ethyl formate (0.85 g, 11.5 mmol) dropwise to a stirred suspension of sodium hydride (0.41 g of 60%, 10 mmol) in tetrahydrofuran (4.5 mL). Reaction was rapid and exothermic. After heating in an oil bath at 50° C. for 20 min., the mixture was carefully acidified with dilute HCl and extracted with ethyl acetate. Extracts were washed with water, saturated NaCl solution, dried (MgSO4) and stripped to give 0.96 g (86%) of off-white solid, m. p. 148-153° C., Rf 0.5 (silica gel, ethanol:ethyl acetate:hexane=1:4:4).

Workup

  1. customReaction
  2. extractionextracted with ethyl acetate
  3. washExtracts were washed with water, saturated NaCl solution
  4. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-fdfb907184ad41d7ac78e4602fd13c19
Source dataset
uspto-grants-2012_04
Patent number
US08153688B2

Reaction notes

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