Acetic Acid → Methyl 2-cyano-3-phenylbutyrate

HRID 1981282Notes

Reaction equation

HRID 1981282 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)[CH3:9].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1.[Pd].O>[C:1]([CH:3]([CH:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:9])[C:4]([O:6][CH3:7])=[O:5])#[N:2]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 7410AcetophenoneHCID 7747Methyl cyanoacetateHCID 517165Ammonium Acetate

Product 1

HCID 13276234Methyl 2-cyano-3-phenylbutyrate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of methyl cyanoacetate (198 g, 2.0 moles), acetophenone (240 g, 2.0 moles), ammonium acetate (30.8 g, 0.4 moles) and acetic acid (96 g, 1.60 moles) in toluene was refluxed with a Dean and Stark trap until water separation ceased (about 4 hours). The resulting Knoevenagel adduct was cooled and stirred under hydrogen (60 psig) with 5% palladium on carbon (8 g) for 2 days. The solution was then depressurized, degassed, filtered and evaporated. The liquid residue was distilled and the fraction with bp 110°-140° C. (about 0.03 mm) collected as mixed stereoisomers of methyl 2-cyano-3-phenylbutyrate as identified by the nmr spectrum.

Workup

  1. custom(about 4 hours)
  2. temperatureThe resulting Knoevenagel adduct was cooled
  3. customdegassed
  4. filtrationfiltered
  5. customevaporated
  6. distillationThe liquid residue was distilled
  7. customthe fraction with bp 110°-140° C. (about 0.03 mm) collected
  8. additionas mixed stereoisomers of methyl 2-cyano-3-phenylbutyrate

Sources & evidence

ORD record
ord-ae70ed403c8c406bafb60517d1aba782
Source dataset
uspto-grants-1985_04
Patent number
US04514340

Reaction notes

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