Acetonitrile → 4-Chlorobenzoylacetonitrile

HRID 2059229Notes

Reaction equation

HRID 2059229 reaction equation
[H-].[Na+].C1COCC1.C(O[C:11](=[O:19])[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)C.[C:20](#[N:22])[CH3:21]>CCOCC>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([C:11]([CH2:21][C:20]#[N:22])=[O:19])=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 81785Ethyl 4-chlorobenzoate

Product 1

HCID 1383084-Chlorobenzoylacetonitrile

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 50% oil dispersion of NaH (24 grams) was placed in a 2 l. 3-necked flask and covered with 250 ml. THF. After heating to reflux, a solution composed of 55 ml. THF, ethyl-4-chlorobenzoate (57 grams), and acetonitrile (20.5 grams) was added in dropwise fashion. The reaction mixture started to solidify after the reactants were added so an additional 200 ml. of THF was added. The mixture was then heated to reflux for 21/2 hours, cooled to room temperature, treated with 1 l. ether, and allowed to stand for 72 hours.

Workup

  1. custom3-necked flask and covered with 250 ml
  2. temperatureAfter heating
  3. temperatureto reflux
  4. additionwere added so an additional 200 ml
  5. temperatureThe mixture was then heated
  6. temperatureto reflux for 21/2 hours
  7. additiontreated with 1 l

Sources & evidence

ORD record
ord-bfcba35cd641438abd8b2c73a200e468
Source dataset
uspto-grants-1982_03
Patent number
US04322429

Reaction notes

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