4-Aminophenol → HCID 178442873, compound

HRID 398757Notes

Reaction equation

HRID 398757 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.CC(CC)=O.[CH2:14]([CH:32]1[CH2:37][C:36](=[O:38])[O:35][C:33]1=[O:34])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].N#N>COCCOCCOC>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]=[C:33]([OH:34])[CH:32]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:37][C:36]([OH:38])=[O:35])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 4034-AminophenolHCID 947NitrogenHCID 6569Methyl Ethyl KetoneHCID 965622,5-Furandione, dihydro-3-octadecyl-

Product 1

HCID 178442873HCID 178442873, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

3.7 Grams of 4-aminophenol and 80 ml of ethyl methyl ketone were charged in a 300 ml flask equipped with a stirrer and a condenser and stirred in an atmosphere of room temperature. Thereto was added 12.0 g of powdery n-octadecylsuccinic anhydride little by little in several parts, followed by stirring at 70°-75° C. for 1 hour. Then, 120 ml of diglyme was added thereto, followed by heating with gently passing N2 gas to first distill off ethyl methyl ketone and then slowly distill off diglyme. After distilling off most of diglyme (the time required: about 3 hours), 120 ml of toluene was added to the residue, followed by leaving to cool. The precipitated crystal was filtered off and washed. The crystal was recrystallized from n-propanol to obtain 10.6 g of the desired product. m.p. 133°-134° C.

Workup

  1. customequipped with a stirrer and a condenser
  2. stirringby stirring at 70°-75° C. for 1 hour
  3. distillationto first distill off ethyl methyl ketone
  4. distillationslowly distill off diglyme
  5. distillationAfter distilling off most of diglyme (the time
  6. additionabout 3 hours), 120 ml of toluene was added to the residue
  7. customby leaving
  8. temperatureto cool
  9. filtrationThe precipitated crystal was filtered off
  10. washwashed
  11. customThe crystal was recrystallized from n-propanol

Sources & evidence

ORD record
ord-fc57f83b79fe447a983d650c1c18858f
Source dataset
uspto-grants-1998_10
Patent number
US05817599

Reaction notes

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