Hydrochloric Acid → 2-Formyl-2-phenylacetonitrile

HRID 1437619Notes

Reaction equation

HRID 1437619 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-d1e1b0f8a70c47518c03f397c78b3987
Source dataset
uspto-grants-2009_11
Patent number
US07622504B2

Reaction notes

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