Acetic Acid → HCID 86742414, compound

HRID 622147Notes

Reaction equation

HRID 622147 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[CH:16]=[CH:15][C:14](O)=[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:27])C>>[O:22]=[C:21]1[CH:20]=[CH:19][C:18](=[O:23])[N:1]1[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2([OH:27])[CH:16]=[CH:15][CH:14]=[CH:13][CH2:12]2)([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 7923Maleic AnhydrideHCID 11148864Phenol, 4-[1-(4-aminophenyl)-1-methylethyl]-

Product 1

HCID 86742414HCID 86742414, compound

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-methyl-ethyl)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-07b91d1e7b944f3e9f5b579b0f4c7425
Source dataset
uspto-grants-1988_09
Patent number
US04769440

Reaction notes

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