Ethyl Acetate → HCID 136124232, compound

HRID 652794Notes

Reaction equation

HRID 652794 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].Cl.[NH2:25][NH:26][C:27]([NH2:29])=[O:28].C(OCC)(=O)C>N1C=CC=CC=1>[C:20]([C:17]1[CH:16]=[C:7]([CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[C:18]=1[OH:19])[C:8](=[N:25][NH:26][C:27]([NH2:29])=[O:28])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:21])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11236Semicarbazide hydrochlorideHCID 1898376Methanone, [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]phenyl-

Product 1

HCID 136124232HCID 136124232, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1.60 g of 3,5-di-t-butyl-4-hydroxybenzophenone and 0.67 g of semicarbazide hydrochloride were dissolved in 12 ml of pyridine, and the solution was refluxed for 6 hours. After the reaction, ethyl acetate was added to the reaction mixture, and the mixture was washed with 5% hydrochloric acid and water and dried. The solvent was removed by concentration, and the residue was chromatographed on a silica gel column and recrystallized from diethyl ether to give 3,5-di-t-butyl-4-hydroxybenzophenone semicarbazone.

Workup

  1. temperaturethe solution was refluxed for 6 hours
  2. additionwas added to the reaction mixture
  3. washthe mixture was washed with 5% hydrochloric acid and water
  4. customdried
  5. customThe solvent was removed by concentration
  6. customthe residue was chromatographed on a silica gel column
  7. customrecrystallized from diethyl ether

Sources & evidence

ORD record
ord-c493b58f55c746efa9bd90067b53e74b
Source dataset
uspto-grants-1987_06
Patent number
US04673692

Reaction notes

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