Methyl Acrylate → Heptanedioic acid, 4-(4-chlorophenyl)-4-cyano-, dimethyl ester

HRID 1576194Notes

Reaction equation

HRID 1576194 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]#[N:10])=[CH:4][CH:3]=1.[C:11]([O:15][CH3:16])(=[O:14])[CH:12]=[CH2:13]>C(O)(C)(C)C>[CH3:16][O:15][C:11](=[O:14])[CH2:12][CH2:13][C:8]([C:9]#[N:10])([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH2:13][CH2:12][C:11]([O:15][CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 12230231Heptanedioic acid, 4-(4-chlorophenyl)-4-cyano-, dimethyl esterYield 71.4%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 25 g. (0.165 mole) of the known compound (p-chlorophenyl)acetonitrile and 77 ml. of methyl acrylate in 80 ml. of t-butyl alcohol is heated to reflux. The heat is removed and 25 ml. of 40% methanolic Triton B in 37 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 0.35 mm. to give 38.06 g. (71.4% yield) of dimethyl-4-cyano-4-(4-chlorophenyl)pimelate, having a boiling point of 186° to 191°C. The nuclear magnetic resonance (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 38.06 g

Sources & evidence

ORD record
ord-4f478072ad414c9b84d7a756918afca8
Source dataset
uspto-grants-1976_09
Patent number
US03979444

Reaction notes

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