Methanol → Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-

HRID 2291392Notes

Reaction equation

HRID 2291392 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:24]#[N:25])([CH2:18][CH2:19][C:20]([O:22]C)=O)[CH2:12][CH2:13]C(OC)=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H-].[Na+].CO>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2([C:24]#[N:25])[CH2:12][CH2:13][C:20](=[O:22])[CH2:19][CH2:18]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 1803855Dimethyl 4-cyano-4-(3,4-dimethoxyphenyl)heptanedioate

Product 1

HCID 749913Cyclohexanecarbonitrile, 1-(3,4-dimethoxyphenyl)-4-oxo-

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of dimethyl 4-(3,4-dimethoxyphenyl)-4-cyanopimelate (11.2 g, 32.1 mmol), sodium hydride (2.31 g, 48.1 mmol) and methanol (1 ml) in 250 ml anhydrous toluene was heated at reflux for 10 hours, cooled to 25° C., quenched with 4 ml acetic acid, washed with H2O, alkali, and brine and dried with MgSO4. The volatiles were removed in vacuo. The residue was recrystallized with hexanes-ethyl acetate. This intermediate was heated at reflux in ethanol, concentrated HCl and 25% aqueous H2SO4 for 10 hours. The volatiles were removed in vacuo. The residue was diluted with water and extracted with ether. The combined organic extracts were washed with water, brine and dried (MgSO4). The volatiles were removed in vacuo. The residue was recrystallized with toluene and then with hexanes-ethyl acetate, mp 111°-12° C. ##STR5##

Workup

  1. temperatureat reflux for 10 hours
  2. customquenched with 4 ml acetic acid
  3. washwashed with H2O
  4. dry with materialbrine and dried with MgSO4
  5. customThe volatiles were removed in vacuo
  6. customThe residue was recrystallized with hexanes-ethyl acetate
  7. temperatureThis intermediate was heated
  8. temperatureat reflux in ethanol
  9. customThe volatiles were removed in vacuo
  10. additionThe residue was diluted with water
  11. extractionextracted with ether
  12. washThe combined organic extracts were washed with water, brine
  13. dry with materialdried (MgSO4)
  14. customThe volatiles were removed in vacuo
  15. customThe residue was recrystallized with toluene

Sources & evidence

ORD record
ord-a30828d51c454d2f8bce6a910e12d36f
Source dataset
uspto-grants-1989_01
Patent number
US04795757

Reaction notes

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