Methyl Methacrylate → Heptanedioic acid, 4-cyano-4-(4-methoxyphenyl)-, dimethyl ester

HRID 1576196Notes

Reaction equation

HRID 1576196 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]#[N:11])=[CH:5][CH:4]=1.[C:12]([O:17][CH3:18])(=[O:16])[C:13](C)=[CH2:14]>C(O)(C)(C)C>[CH3:18][O:17][C:12](=[O:16])[CH2:13][CH2:14][C:9]([C:10]#[N:11])([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH2:14][CH2:13][C:12]([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 6658Methyl MethacrylateHCID 66031Benzeneacetonitrile, 4-methoxy-

Product 1

HCID 12230232Heptanedioic acid, 4-cyano-4-(4-methoxyphenyl)-, dimethyl esterYield 70.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 36.75 g. (0.25 mole) of the known compound (p-methoxyphenyl)acetonitrile and 116 ml. of methyl methacrylate in 120 ml. of t-butyl alcohol is heated to reflux. The heat is removed and 38 ml. of 40% methanolic Triton B in 56 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 0.6 to 0.75 mm. to give 55.9 g. (70.2% yield) of dimethyl-4-cyano-4-(4-methoxyphenyl)pimelate, having a boiling point of 205° to 210°C. The NMR spectrum of the compound confirms its expected structure.

Workup

  1. additionA mixture of 36.75 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 55.9 g

Sources & evidence

ORD record
ord-3437f9a2ff7c4a52882ad7016a10d450
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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