1,1-Dimethylhydrazine → HCID 136166736, compound

HRID 652792Notes

Reaction equation

HRID 652792 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:18]=1[OH:19])[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O)([CH3:4])([CH3:3])[CH3:2].[CH3:24][N:25]([CH3:27])[NH2:26].C1(C)C=CC(S(O)(=O)=O)=CC=1>O>[CH3:24][N:25]([CH3:27])[N:26]=[C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:18]([OH:19])=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:16]=1

Participants

5

Reactant 3

HCID 59761,1-DimethylhydrazineHCID 6101p-Toluenesulfonic acidHCID 1898376Methanone, [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]phenyl-

Product 1

HCID 136166736HCID 136166736, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

One gram of 3,5-di-t-butyl-4-hydroxybenzophenone was added to 2 ml of 1,1-dimethylhydrazine, and the mixture was heated at 70° to 75° C. for 8 hours in the presence of 20 mg of p-toluenesulfonic acid in autoclave. After cooling, the reaction mixture was poured into water and extracted with diethyl ether. The ethereal layer was washed with water and dried. The ether was distilled, and the residue was chromatographed on a silica gel column, and recrystallized from diethyl ether to give 3,5-di-t-butyl-4-hydroxybenzophenone dimethylhydrazone as pale yellow needles.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with diethyl ether
  3. washThe ethereal layer was washed with water
  4. customdried
  5. distillationThe ether was distilled
  6. customthe residue was chromatographed on a silica gel column
  7. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-54c54bad9082412b9192c9549d67a5bf
Source dataset
uspto-grants-1987_06
Patent number
US04673692

Reaction notes

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