Toluene → HCID 19978531, compound

HRID 1089866Notes

Reaction equation

HRID 1089866 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=O)[CH:3]=[CH:2]1.C1(C)C=CC=CC=1.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)([CH3:24])[CH3:23])=[CH:18][CH:17]=1.C(O)(C)C>S(=O)(=O)(O)O.O>[OH:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([C:25]2[CH:26]=[CH:27][C:28]([N:31]3[C:1](=[O:7])[CH:2]=[CH:3][C:4]3=[O:6])=[CH:29][CH:30]=2)([CH3:24])[CH3:23])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 3776IsopropanolHCID 7923Maleic AnhydrideHCID 11148864Phenol, 4-[1-(4-aminophenyl)-1-methylethyl]-

Product 1

HCID 19978531HCID 19978531, compoundYield 478.3%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 962WaterSolvent

Procedure

To a reaction vessel equipped with a stirrer, thermometer and an azeotropic distillation trap, 60 g (0.1 mole) of maleic anhydride, 480 g of toluene and 2.6 g of 95% sulfuric acid were charged and heated to a reflux temperature. A solution containing 114 g (0.5 mole) of 2-(4-hydroxyphenyl)-2-(4-aminophenyl)propane in 160 g of N,N'-dimethylacetamide was dropwise added from a dropping funnel over 4 to 5 hours and reacted for 5 hours at the same temperature. Generated water by the reaction was removed by azeotropic distillation. After completing the reaction, the reaction mixture was cooled to 80° to 90° C. and the solvent was successively removed under reduced pressure. The organic layer thus obtained was mixed with 100 ml of isopropyl alcohol and then 300 ml of water was added and stirred for 0.5 to 1 hour to precipitate crystals. The crystals were filtered and dried to obtain 147 g of 2-(4-hydroxyphenyl)-2-(4-maleimidophenyl)propane as yellow crystals. The yield was 96%.

Workup

  1. customTo a reaction vessel equipped with a stirrer
  2. temperatureheated to a reflux temperature
  3. additionwas dropwise added from a dropping funnel over 4 to 5 hours
  4. customreacted for 5 hours at the same temperature
  5. customGenerated water by the reaction was removed by azeotropic distillation
  6. customthe reaction
  7. temperaturethe reaction mixture was cooled to 80° to 90° C.
  8. customthe solvent was successively removed under reduced pressure
  9. customThe organic layer thus obtained
  10. customto precipitate crystals
  11. filtrationThe crystals were filtered
  12. customdried

Sources & evidence

ORD record
ord-6b98322b84b140c8be2bd0c3e57d0e05
Source dataset
uspto-grants-1992_01
Patent number
US05079331

Reaction notes

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