Hydrochloric Acid → 2-(4-Chloro-2,6-dimethylphenyl)-3-oxobutanenitrile

HRID 842009Notes

Reaction equation

HRID 842009 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH2:9][C:10]#[N:11])=[C:4]([CH3:12])[CH:3]=1.[Na].Cl.[CH3:15][CH2:16][O:17]C(C)=O>>[Cl:1][C:2]1[CH:3]=[C:4]([CH3:12])[C:5]([CH:9]([C:16](=[O:17])[CH3:15])[C:10]#[N:11])=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 5360545SodiumHCID 695455384-Chloro-2,6-dimethylbenzeneacetonitrile

Product 1

HCID 184069852-(4-Chloro-2,6-dimethylphenyl)-3-oxobutanenitrile

Conditions

Temperature
90 °C

Procedure

Dissolve 4-chloro-2,6-dimethyl phenyl acetonitrile (2.3 g, 179.2 g/mol) in 15 mL EtOAc and add sodium metal (0.35 g, pea-sized fragments). Heat to reflux (90° C. bath temperature) under N2 overnight. Evaporate down to solid and slurry up in Et2O (100 mL); stir vigorously to break up fragments. Filter and wash solid with copious amounts of Et2O. Dissolve solid in H2O to form a clear yellow solution, and add 1.0 N HCl (100 mL) to pH 1. Extract the resulting cloudy solution with CH2Cl2 (3×100 mL) until aqueous layer is clear. Pool and dry the organic layers over Na2SO4, filter and evaporate to yellow oil (1.8 g). TLC: Rf=0.2 using 20% EtOAc/80% hexanes as eluent. LCMS=222.3 (MH+); 220.2 (M−)

Workup

  1. temperatureHeat
  2. customEvaporate down to solid
  3. filtrationFilter
  4. washwash solid with copious amounts of Et2O
  5. dissolutionDissolve solid in H2O
  6. customto form a clear yellow solution
  7. extractionExtract the resulting cloudy solution with CH2Cl2 (3×100 mL) until aqueous layer
  8. dry with materialPool and dry the organic layers over Na2SO4
  9. filtrationfilter
  10. customevaporate to yellow oil (1.8 g)

Sources & evidence

ORD record
ord-e4e79a3ddbeb404b8cecc99b724d775e
Source dataset
uspto-grants-2002_04
Patent number
US06372743B1

Reaction notes

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