Acetic Acid → 2-Cyano-4-(4-methoxy-phenyl)-3-methyl-but-2-enoic Acid Ethyl Ester

HRID 1860680Notes

Reaction equation

HRID 1860680 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10](=O)[CH3:11])=[CH:5][CH:4]=1.[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:19]([O:18][C:16](=[O:17])[C:15]([C:13]#[N:14])=[C:10]([CH3:11])[CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:20]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 312311-(p-Methoxyphenyl)-2-propanoneHCID 517165Ammonium Acetate

Product 1

HCID 600747842-Cyano-4-(4-methoxy-phenyl)-3-methyl-but-2-enoic Acid Ethyl EsterYield 64.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flask equipped with a Dean-stark trap was prepared a solution of 1-(4-Methoxy-phenyl)-propan-2-one (40 g), ethyl cyanoacetate (27.56 g), ammonium acetate (9.40 g), acetic acid (14.64 g) and toluene (150 ml) at room temperature. The solution was heated to reflux overnight. The solution was cooled to room temperature, washed with water and brine, and concentrated. The crude product was purified on a silica gel column, eluting with 10% ethyl acetate/hexane to afford colorless oil (40.76 g). The 1H NMR was consistent with the proposed structure.

Workup

  1. customIn a flask equipped with a Dean-stark trap
  2. temperatureThe solution was heated
  3. temperatureto reflux overnight
  4. washwashed with water and brine
  5. concentrationconcentrated
  6. customThe crude product was purified on a silica gel column
  7. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-445044ea221c4ecf8a52f50358bcbc5f
Source dataset
uspto-grants-2003_03
Patent number
US06531494B1

Reaction notes

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