Methylparaben → 4-(4-(1,1,3-Trimethyl-2-cyclohexyl)-butoxy)-benzoic acid methyl ester

HRID 2165178Notes

Reaction equation

HRID 2165178 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+].[CH3:22][C:23]1([CH3:35])[CH2:28][CH2:27][CH2:26][CH:25]([CH3:29])[CH:24]1[CH2:30][CH2:31][CH:32](Cl)[CH3:33]>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][CH2:33][CH2:32][CH2:31][CH2:30][CH:24]2[CH:25]([CH3:29])[CH2:26][CH2:27][CH2:28][C:23]2([CH3:22])[CH3:35])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 7456MethylparabenHCID 13387N-methyl-2-pyrrolidoneHCID 10942334Sodium MethoxideHCID 144574904-(1,1,3-Trimethyl-2-cyclohexyl)-2-butyl chloride

Product 1

HCID 572346844-(4-(1,1,3-Trimethyl-2-cyclohexyl)-butoxy)-benzoic acid methyl ester

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 887MethanolSolvent2×

Procedure

Methanol was removed by distillation from a mixture of 11.7 g (77 mmol) 4-hydroxybenzoic acid methyl ester, 200 ml N-methylpyrrolidone, and I3.8 g (77 mmol) 30% sodium methylate solution in methanol, then 0.6 g tetrabutylammonium iodide and 20.0 g (92 mmol) 4-(1,1,3-trimethyl-2-cyclohexyl)-2-butyl chloride were added. This was followed by heating with stirring for 8 hours to 160° C. After cooling to room temperature, the reacted solution was filtered off from the sodium chloride formed, concentrated to dryness under reduced pressure, the evaporation residue was 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 7:3). 13.9 g (54% of the theoretical) of 4-(4-(1,1,3-trimethyl-2-cyclohexyl)-butoxy)-benzoic acid methyl ester were obtained in the form of a colorless oil having a refractive index at 20° C. of 1.5197.

Workup

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

Sources & evidence

ORD record
ord-318b012a7c91428b80ce5c49e8b3d042
Source dataset
uspto-grants-1990_07
Patent number
US04939171

Reaction notes

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