Methyl Acrylate → dimethyl 4-cyano-4-phenylheptanedioate

HRID 1948586Notes

Reaction equation

HRID 1948586 reaction equation
[C:1]1([CH2:7][C:8]#[N:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O:14][CH3:15])(=[O:13])[CH:11]=[CH2:12]>C(O)(C)(C)C>[CH3:15][O:14][C:10](=[O:13])[CH2:11][CH2:12][C:7]([C:8]#[N:9])([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH2:12][CH2:11][C:10]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 7294Methyl AcrylateHCID 8794Phenylacetonitrile

Product 1

HCID 283742dimethyl 4-cyano-4-phenylheptanedioate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Phenylacetonitrile (11.7 g, 0.1 mole) and methyl acrylate (47 ml, 0.5 mole) were added to tert-butanol (60 ml) and heated to boiling point. The source of heat was then removed. Triton B (benzyltrimethylammonium hydroxide, 40% in methanol, 15.2 ml) dissolved in tert-butanol (23 ml) was added dropwise, first of all slowly and then at a faster rate. After the dropwise addition the reaction mixture was boiled under reflux for 4 hours. The reaction mixture was cooled to room temperature overnight. The reaction mixture was worked up by adding toluene (100 ml) and water (70 ml). The organic phase was separated and washed with water (1×70 ml) and saturated sodium chloride solution (1×50 ml). After drying over Na2SO4, the solvent was distilled off in a fume cupboard on account of the strong smell. Purification was carried out by bulb tube distillation at a pressure of 7.8×10−2 mbar and at a temperature of 235° C. The desired 4-cyano-4-phenylheptanedioic acid dimethyl ester was obtained in a yield of 21.45 g (72%) as a colourless viscous substance.

Workup

  1. temperatureheated
  2. temperatureThe source of heat
  3. customwas then removed
  4. dissolutionTriton B (benzyltrimethylammonium hydroxide, 40% in methanol, 15.2 ml) dissolved in tert-butanol (23 ml)
  5. additionwas added dropwise
  6. additionAfter the dropwise addition the reaction mixture
  7. temperatureunder reflux for 4 hours
  8. additionby adding toluene (100 ml) and water (70 ml)
  9. customThe organic phase was separated
  10. washwashed with water (1×70 ml) and saturated sodium chloride solution (1×50 ml)
  11. dry with materialAfter drying over Na2SO4
  12. distillationthe solvent was distilled off in a fume cupboard on account of the strong smell
  13. customPurification
  14. customwas carried out by bulb tube
  15. distillationdistillation at a pressure of 7.8×10−2 mbar
  16. customat a temperature of 235° C

Sources & evidence

ORD record
ord-9bdfa22de7f742878bbf9360501cfab1
Source dataset
uspto-grants-2013_03
Patent number
US08399503B2

Reaction notes

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