Potassium Hydroxide → HCID 86631894, compound

HRID 1163465Notes

Reaction equation

HRID 1163465 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)=[O:4].[OH-].[K+].[N:22]1[N:23]([C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=2[O-:38])[N:24]=[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=12>C(#N)C>[N:22]1[N:23]([C:31]2[CH:36]=[C:35]([CH3:37])[CH:34]=[CH:33][C:32]=2[O:38][CH2:2][C:3]([C:5]2[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=2)=[O:4])[N:24]=[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=12

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-oneHCID 4318465HCID 4318465, compound

Product 1

HCID 86631894HCID 86631894, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.54 g (20 mmol) of 2-bromo-1-(4-hydroxy-3,5-di-tert-butylphenyl)-ethanone and 1.98 g (30 mmol) of potassium hydroxide are dissolved in 150 ml of acetonitrile and stirred under inert atmosphere at room temperature for 30 minutes. Then 5.27 g (20 mmol) of 2-benzotriazol-2-yl-4-methyl-phenolate is added in portions. Stirring at room temperature is continued for additional 3 hours. After adjusting the pH to 6-7 the mixture is extracted with ethyl acetate. The collected organic phases are washed with water, dried and evaporated. Crystallization of the crude product from methanol gives 6.85 g of compound 106, m.p. 155-157° C.

Workup

  1. stirringStirring at room temperature
  2. waitis continued for additional 3 hours
  3. extractionis extracted with ethyl acetate
  4. washThe collected organic phases are washed with water
  5. customdried
  6. customevaporated
  7. customCrystallization of the crude product from methanol

Sources & evidence

ORD record
ord-3c7cfe88f02a41639a25cc81b36a4663
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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