N-methyl-2-pyrrolidone → 4Isononyloxycinnamic acid methyl ester

HRID 2165824Notes

Reaction equation

HRID 2165824 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.CN1CCCC1=O.C[O-].[Na+].[CH2:24](Cl)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31]>CO.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 92203Methyl p-coumarateHCID 10942334Sodium MethoxideHCID 15918114Isononyl chloride

Product 1

HCID 543993024Isononyloxycinnamic acid methyl ester

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 887MethanolSolvent2×

Procedure

Methanol was removed by distillation from a mixture of 14.2 g (79.7 mmol) 4-hydroxycinnamic acid methyl ester, 150 ml N-methylpyrrolidone and 14.4 g (79.7 mmol) 30% sodium methylate solution in methanol, then 0.5 g tetrabutylammonium chloride and 15.5 g (95.6 mmol) isononyl chloride were added. The addition was followed by heating with stirring for 8 hours to 160 C. After cooling to room temperature, the solution was filtered off from the sodium chloride formed, concentrated to dryness under reduced pressure, the evaporation residue taken up in methylene chloride, washed with water, dried with sodium sulfate and, after concentration by evaporation, chromatographed on silica gel (Merck) (eluent: methylene chloride/toluene =8.2). 20.1 g (91% of the theoretical) 4isononyloxycinnamic acid methyl ester were obtained in the form of a colorless oil having a refractive index at 20 C of 1.5414.

Workup

  1. additionThe addition
  2. temperatureby heating
  3. filtrationthe solution was filtered off from the sodium chloride
  4. customformed
  5. concentrationconcentrated to dryness under reduced pressure
  6. washwashed with water
  7. dry with materialdried with sodium sulfate
  8. concentrationafter concentration
  9. customby evaporation
  10. customchromatographed on silica gel (Merck) (eluent: methylene chloride/toluene =8.2)

Sources & evidence

ORD record
ord-9e0a72af0b83451eb37fd2ecfe865d1b
Source dataset
uspto-grants-1990_07
Patent number
US04942174

Reaction notes

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