Methyl Acrylate → Dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioate

HRID 1576197Notes

Reaction equation

HRID 1576197 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:14]([O:18][CH3:19])(=[O:17])[CH:15]=[CH2:16]>C(O)(C)(C)C>[CH3:19][O:18][C:14](=[O:17])[CH2:15][CH2:16][C:11]([C:12]#[N:13])([C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)[CH2:16][CH2:15][C:14]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 667273,4-Dimethoxybenzeneacetonitrile

Product 1

HCID 1803855Dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioateYield 65.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 25 g. (0.141 mole) of the known compound (3,4-dimethoxyphenyl)acetonitrile and 66 ml. of methyl acrylate in 70 ml. of t-butyl alcohol is heated to reflux. The heat is removed and 21.5 ml. of 40% methanolic Triton B in 32 ml. of t-butyl alcohol quickly added. After about 4 hours of heating at reflux the mixture is allowed to cool and taken up in water and benzene. The organic layer is washed successively with 2.5 N hydrochloric acid, water and brine and then evaporated to dryness. The residue is distilled under vacuum, first at 40 mm. of mercury to remove excess methyl acrylate and then at 0.20 mm. to give 32.22 g. (65.4% yield) of dimethyl-4-cyano-4-(3,4-dimethoxyphenyl)pimelate, having a boiling point of 210° to 214°C. The NMR spectrum of the compound confirms its expected structure.

Workup

  1. additionA mixture of 25 g
  2. customThe heat is removed
  3. additionof t-butyl alcohol quickly added
  4. temperatureAfter about 4 hours of heating
  5. temperatureat reflux the mixture
  6. temperatureto cool
  7. washThe organic layer is washed successively with 2.5 N hydrochloric acid, water and brine
  8. customevaporated to dryness
  9. distillationThe residue is distilled under vacuum, first at 40 mm
  10. customof mercury to remove excess methyl acrylate
  11. customto give 32.22 g

Sources & evidence

ORD record
ord-0cec7b7a511f4a2d9fa27973322a5fc1
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

Loading…