Toluene → 4-(2-Hydroxy-4,5-dimethylbenzyl)-2,5-dimethylphenol

HRID 361977Notes

Reaction equation

HRID 361977 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:12]1([OH:20])[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=1.C1(C)C=CC=CC=1.O[CH2:29][C:30]1[C:35]([CH3:36])=[CH:34][C:33]([OH:37])=[C:32]([CH3:38])[CH:31]=1>O.C(OCC)(=O)C>[OH:20][C:12]1[CH:13]=[C:14]([CH3:19])[C:15]([CH3:18])=[CH:16][C:17]=1[CH2:29][C:30]1[C:35]([CH3:36])=[CH:34][C:33]([OH:37])=[C:32]([CH3:38])[CH:31]=1

Participants

7

Reactant 4

HCID 1140Toluene2×HCID 6101p-Toluenesulfonic acidHCID 72493,4-DimethylphenolHCID 109426404-Hydroxymethyl-2,5-dimethylphenol

Product 1

HCID 540565984-(2-Hydroxy-4,5-dimethylbenzyl)-2,5-dimethylphenolYield 68.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

Into a 1 liter of four-necked flask were charged 1.90 g of para-toluene sulfonic acid, 24.43 g of 3,4-xylenol and 48.87 g of toluene. Further, keeping the temperature at 30° C., 7.61 g of 4-hydroxymethyl-2,5-dimethylphenol was added in ten portions over 1 hour. The mixture was stirred at the same temperature for 2 more hours. After completion of the reaction, 50 g of toluene and 50 g of ethyl acetate was added. Thereafter, 50 g of deionized water was added and the resulting mixture was stirred and a phase separation was carried out. Then, metal content was removed by adding 50 g of 1% aqueous oxalic acid solution, followed by stirring the mixture and by carrying out a phase separation. Thereafter, washing with 50 g of deionized water was repeated four times, and the oil phase was concentrated. To the concentrated mass, 100 g of toluene was added and the resulting solution was cooled to 20° C. and filtered. The filter cake was rinsed with 200 g of toluene and dissolved in 50 g of ethyl acetate. After adding 200 g of toluene thereto,the resulting mixture was concentrated. To the concentrated mass, 100 g of toluene was added and the resulting mass was cooled to 20° C. and filtered. The filter cake was rinsed with 100 g of toluene and dried a whole day and night under reduced pressure at 45 ° C. to obtain 8.82 g of 4-(2-hydroxy-4,5-dimethylbenzyl)-2,5-dimethylphenol.

Workup

  1. customat 30° C.
  2. additionwas added
  3. stirringthe resulting mixture was stirred
  4. customa phase separation
  5. customThen, metal content was removed
  6. additionby adding 50 g of 1% aqueous oxalic acid solution
  7. stirringby stirring the mixture
  8. customa phase separation
  9. washThereafter, washing with 50 g of deionized water
  10. concentrationthe oil phase was concentrated
  11. additionTo the concentrated mass, 100 g of toluene was added
  12. filtrationfiltered
  13. washThe filter cake was rinsed with 200 g of toluene
  14. dissolutiondissolved in 50 g of ethyl acetate
  15. additionAfter adding 200 g of toluene
  16. customthereto,the resulting mixture
  17. concentrationwas concentrated
  18. additionTo the concentrated mass, 100 g of toluene was added
  19. temperaturethe resulting mass was cooled to 20° C.
  20. filtrationfiltered
  21. washThe filter cake was rinsed with 100 g of toluene
  22. customdried a whole day and night under reduced pressure at 45 ° C.

Sources & evidence

ORD record
ord-51765a1d10a84f428d5236e02478bee7
Source dataset
uspto-grants-1999_02
Patent number
US05866724

Reaction notes

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