Acetic Acid → 1,4-Bis(2-carbethoxy-2-cyano-1-methylethenyl)benzene

HRID 444126

Reaction equation

HRID 444126 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH3:11])=[CH:6][CH:5]=1)(=O)[CH3:2].[C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])#[N:14].[C:21]([O-:24])(=[O:23])[CH3:22].[NH4+:25].[C:26](O)(=O)[CH3:27].[C:30]1(C)C=CC=CC=1>O>[C:16]([C:15]([C:13]#[N:14])=[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:11])=[C:22]([C:30]#[N:25])[C:21]([O:24][CH2:26][CH3:27])=[O:23])=[CH:6][CH:5]=1)[CH3:2])([O:18][CH2:19][CH3:20])=[O:17]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 1140TolueneHCID 7764Ethyl cyanoacetateHCID 138881,4-DiacetylbenzeneHCID 517165Ammonium Acetate

Product 1

HCID 33932701,4-Bis(2-carbethoxy-2-cyano-1-methylethenyl)benzene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of p-diacetylbenzene (20.25 g, 0.125 mole), ethyl cyanoacetate (28.3 g, 0.25 mole), ammonium acetate (3.85 g) and acetic acid (10 g) was combined in a 500 ml glass round-bottom flask with toluene (150 ml) and refluxed for 12 hours. A Dean-Stark trap was employed to trap water formed during the reaction. Refluxing was discontinued and the solvent evaporated. The residue containing crude product was distilled under reduced pressure. One fraction, boiling point range 177° C.-195° C. (0.6 mm) amounting to 20.6 g was identified as predominately the 1:1 condensation product. A second fraction, boiling point ~200° C. yielded 18.2 g of 1,4-bis(2-carbethoxy-2-cyano-1-methylethenyl)benzene.

Workup

  1. temperaturerefluxed for 12 hours
  2. customA Dean-Stark trap was employed to trap
  3. temperatureRefluxing
  4. customthe solvent evaporated
  5. additionThe residue containing crude product
  6. distillationwas distilled under reduced pressure
  7. custompoint range 177° C.-195° C. (0.6 mm) amounting
  8. customthe 1:1 condensation product

Sources & evidence

ORD record
ord-d764701e8bc64cfb8a45efabc7211bdc
Source dataset
uspto-grants-1981_04
Patent number
US04263209

Linked notes

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