Dichloromethane → HCID 136393672, compound

HRID 652786Notes

Reaction equation

HRID 652786 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][OH:26].[OH-].[K+].ClCCl>C(O)C>[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](=[N:25][OH:26])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 1898376Methanone, [3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]phenyl-

Product 1

HCID 136393672HCID 136393672, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

12.4 g of 3,5-di-t-butyl-4-hydroxybenzophenone and 3.15 g of hydroxylamine hydrochloride were dissolved in 100 ml of ethanol, and with stirring, a solution of 2.77 g of potassium hydroxide in 20 ml of ethanol was added dropwise at room temperature. The mixture was then refluxed for 24 hours with stirring. After cooling, dichloromethane was added to the reaction mixture. The dichloromethane layer was separated, washed with water, and dried. The solvent was distilled off, and n-hexane was added to the residue. The precipitated crystals were collected by filtration, and recrystallized from ether/n-hexane to give 3,5-di-t-butyl-4-hydroxybenzophenone oxime.

Workup

  1. temperatureThe mixture was then refluxed for 24 hours
  2. stirringwith stirring
  3. temperatureAfter cooling
  4. customThe dichloromethane layer was separated
  5. washwashed with water
  6. customdried
  7. distillationThe solvent was distilled off
  8. additionn-hexane was added to the residue
  9. filtrationThe precipitated crystals were collected by filtration
  10. customrecrystallized from ether/n-hexane

Sources & evidence

ORD record
ord-5d3b0c9d259d4659b91eea4e916ecb27
Source dataset
uspto-grants-1987_06
Patent number
US04673692

Reaction notes

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