Toluene → bis(3,5-Dimethylcyclohexyl)phthalate

HRID 1701464Notes

Reaction equation

HRID 1701464 reaction equation
[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[CH3:12][CH:13]1[CH2:18][CH:17]([CH3:19])[CH2:16][CH:15]([OH:20])[CH2:14]1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24](S(O)(=O)=O)=[CH:23][CH:22]=1.[C:32]1(C)C=CC=CC=1>O>[CH3:12][CH:13]1[CH2:18][CH:17]([CH3:19])[CH2:16][CH:15]([O:20][C:4](=[O:5])[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1]([O:6][CH:23]2[CH2:24][CH:25]([CH3:32])[CH2:26][CH:21]([CH3:31])[CH2:22]2)=[O:11])[CH2:14]1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 6101p-Toluenesulfonic acidHCID 6811Phthalic AnhydrideHCID 215843,5-Dimethylcyclohexan-1-ol

Product 1

HCID 20751009bis(3,5-Dimethylcyclohexyl)phthalate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 ml of toluene was added to a mixture of 44.4 g (0.3 mol) of phthalic anhydride, 83.3 g (0.66 mol) of 3,5-dimethylcyclohexanol and 2 g of p-toluenesulfonic acid and the mixture was refluxed with heating for 12 hours with the azeotropic removal of 6 ml of water. After the reaction, the mixture was cooled and 200 ml of toluene was added to the mixture. The organic solvent layer was washed with water, a 5% aqueous solution of sodium hydroxide and water, in this order and dried with anhydrous sodium sulfate. After filtering the mixture, the filtrate was concentrated under reduced pressure. 50 ml of hexane was added to the concentrate and column chromatographed to obtain the desired compound. The carrier used was 800 g of Silica Gel 60 manufactured by Merck Co. Hexane and hexane-diethyl ether (9:1 in volume ratio) were used as the solvent and 105.7 g (yield 91.2%) of Compound (5) was obtained from the hexane-diethyl ether eluate.

Workup

  1. temperaturethe mixture was refluxed
  2. customAfter the reaction
  3. temperaturethe mixture was cooled
  4. washThe organic solvent layer was washed with water
  5. dry with materiala 5% aqueous solution of sodium hydroxide and water, in this order and dried with anhydrous sodium sulfate
  6. filtrationAfter filtering the mixture
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. addition50 ml of hexane was added to the
  9. concentrationconcentrate
  10. customcolumn chromatographed

Sources & evidence

ORD record
ord-30b75737d8764cd18a84186f1e117dd2
Source dataset
uspto-grants-1980_03
Patent number
US04193802

Reaction notes

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