Maleic Anhydride → HCID 19978531, compound

HRID 620344Notes

Reaction equation

HRID 620344 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1.[C:18]1(=O)[O:23][C:21](=[O:22])[CH:20]=[CH:19]1>C(O)(=O)C>[O:22]=[C:21]1[CH:20]=[CH:19][C:18](=[O:23])[N:1]1[C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)([CH3:10])[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

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

Product 1

HCID 19978531HCID 19978531, compoundYield 51.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
25 °C

Procedure

A 45.46 gram portion of 4-(1-(4-aminophenyl)-1-methylethyl)phenol (0.20 mole) and 500 milliliters of acetic acid were added to a reactor and maintained under a nitrogen atmosphere with stirring. The stirred solution was maintained at 25° C., then 19.61 grams of maleic anhydride (0.20 mole) dissolved in 100 milliliters of acetic acid was added to the reactor and heating to a reflux commenced. The 126° C. reflux temperature was maintained for 15 hours (54,000 s), then the product was dried under vacuum by rotary evaporation at 100° C. for 60 minutes (3600 s). The crude product was dissolved in 250 milliliters of o-dichlorobenzene at 120° C. and then cooled to 25° C. The light yellow colored solution was decanted away from a brown colored oil layer and dried under vacuum by rotary evaporation at 100° C. for 60 minutes (3600 s) to provide 31.4 grams of 4-(1-(4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl)-1-methylethyl)phenol as a bright yellow colored powder. Infrared spectrophotometric analysis of a film sample of the product confirmed the product structure.

Workup

  1. temperaturemaintained under a nitrogen atmosphere
  2. additionwas added to the reactor
  3. temperatureheating to a reflux
  4. temperatureThe 126° C. reflux temperature
  5. temperaturewas maintained for 15 hours (54,000 s)
  6. customthe product was dried under vacuum by rotary evaporation at 100° C. for 60 minutes (3600 s)
  7. dissolutionThe crude product was dissolved in 250 milliliters of o-dichlorobenzene at 120° C.
  8. temperaturecooled to 25° C
  9. customThe light yellow colored solution was decanted away from a brown colored oil layer
  10. customdried under vacuum by rotary evaporation at 100° C. for 60 minutes (3600 s)

Sources & evidence

ORD record
ord-bedc120486234fd8ac4fc051f19cac25
Source dataset
uspto-grants-1989_04
Patent number
US04820798

Reaction notes

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