Methylparaben → HCID 53799950, compound

HRID 2165180Notes

Reaction equation

HRID 2165180 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.CN1CCCC1=O.C[O-].[Na+].[CH2:22](Cl)[CH:23]=[C:24]([CH2:26][CH2:27][CH:28]=[C:29]([CH2:31][CH2:32][CH:33]=[C:34]([CH3:36])[CH3:35])[CH3:30])[CH3:25]>CO.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:22][CH:23]=[C:24]([CH2:26][CH2:27][CH:28]=[C:29]([CH2:31][CH2:32][CH:33]=[C:34]([CH3:35])[CH3:36])[CH3:30])[CH3:25])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 13387N-methyl-2-pyrrolidoneHCID 40734091-Chloro-3,7,11-trimethyldodeca-2,6,10-trieneHCID 10942334Sodium Methoxide

Product 1

HCID 53799950HCID 53799950, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

After removal of the methanol by distillation from a mixture of 20.0 g (131 mmol) 4-hydroxybenzoic acid methyl ester, 200 ml N-methylpyrrolidone, and 25.9 g (144 mmol) 30% sodium methylate solution in methanol, 1.1 g tetrabutylammonium iodide and 38.0 g (158 mmol) farnesyl chloride were added. This was followed by heating with stirring for 7 hours at 160° C. After cooling to room temperature, the solution was filtered off from the sodium chloride formed, evaporated under reduced pressure to dryness, the evaporation residue was taken up in methylene chloride, washed with water, dried with sodium sulfate, distilled under reduced pressure after concentration by evaporation and the fraction boiling at 190° to 202° C. under 0.015 mbar pressure was chromatographed on silica gel (Merck) (eluent: methylene chloride/toluene =7:3). 19.2 g (41% of the theoretical) of 4-farnesyloxybenzoic acid methyl ester was obtained in the form of a colorless oil having a refractive index at 20° C. of 1.5293.

Workup

  1. customAfter removal of the methanol
  2. distillationby distillation
  3. additionwere added
  4. temperatureby heating
  5. temperatureAfter cooling to room temperature
  6. filtrationthe solution was filtered off from the sodium chloride
  7. customformed
  8. customevaporated under reduced pressure to dryness
  9. washwashed with water
  10. dry with materialdried with sodium sulfate
  11. distillationdistilled under reduced pressure
  12. concentrationafter concentration
  13. customby evaporation
  14. customthe fraction boiling at 190° to 202° C. under 0.015 mbar pressure was chromatographed on silica gel (Merck) (eluent: methylene chloride/toluene =7:3)

Sources & evidence

ORD record
ord-4f2ad64a802a425f81f544ab9a7fdbc3
Source dataset
uspto-grants-1990_07
Patent number
US04939171

Reaction notes

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