Hydrochloric Acid → 4-[3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzoyl]benzonitrile

HRID 986682Notes

Reaction equation

HRID 986682 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[C:9]2[CH:14]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[C:12]([OH:19])=[C:11]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:10]=2)=[CH:4][CH:3]=1.[N:25]1C2C(=CC=CC=2)C=C[CH:26]=1.Cl>ClCCl>[C:26]([C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:24])[C:9]2[CH:10]=[C:11]([C:20]([CH3:21])([CH3:22])[CH3:23])[C:12]([OH:19])=[C:13]([C:15]([CH3:16])([CH3:17])[CH3:18])[CH:14]=2)=[CH:4][CH:3]=1)#[N:25]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7047QuinolineHCID 14032766HCID 14032766, compound

Product 1

HCID 140327674-[3,5-Bis(1,1-dimethylethyl)-4-hydroxybenzoyl]benzonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
180 °C

Procedure

A stirred mixture of 52 g (0.13 mole) of 4'-bromo-3,5-di(tertiary-butyl)-4-hydroxybenzophenone, 20 g (0.22 mole) of cuprous cyanide and 150 ml of quinoline was heated at about 180° C. for one day, followed by heating at reflux (235° to 245° C.) for two hours. The cooled solution was mixed with about one liter of 10% aqueous hydrochloric acid, and 400 ml of dichloromethane was added. The solid was separated by filtration, and extracted with additional hydrochloric acid and dichloromethane. The filtrates and washings were combined and the organic layer was separated and evaporated. The residue was recrystallized from a benzene-hexane mixture with treatment with decolorizing charcoal to provide 4'-cyano-3,5-di(tertiary-butyl)-4-hydroxybenzophenone. A further recrystallization from a mixture of ethanol and isopropanol with treatment with decolorizing charcoal provided white needles, m.p. 166.5° to 168° C. Analysis: Calculated for C22H25NO2 : % C, 78.8; %H, 7.5; %N, 4.2; Found; %C, 78.8; %H, 7.5; %N, 4.1.

Workup

  1. temperatureby heating
  2. temperatureat reflux (235° to 245° C.) for two hours
  3. additionwas added
  4. customThe solid was separated by filtration
  5. extractionextracted with additional hydrochloric acid and dichloromethane
  6. customthe organic layer was separated
  7. customevaporated
  8. customThe residue was recrystallized from a benzene-hexane mixture with treatment with decolorizing charcoal

Sources & evidence

ORD record
ord-b8790cb16a624ddb975975664be44b2e
Source dataset
uspto-grants-1987_12
Patent number
US04714776

Reaction notes

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