Hydrochloric Acid → 2-Ethoxy-1-(4-hydroxy-3,5-di-tert-butylphenyl)-ethanone

HRID 1163471Notes

Reaction equation

HRID 1163471 reaction equation
[OH-].[K+].Br[CH2:4][C:5]([C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=1)=[O:6].Cl.[CH2:23]([OH:25])[CH3:24]>>[CH2:23]([O:25][CH2:4][C:5]([C:7]1[CH:12]=[C:11]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:10]([OH:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=1)=[O:6])[CH3:24]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one

Product 1

HCID 577472312-Ethoxy-1-(4-hydroxy-3,5-di-tert-butylphenyl)-ethanone

Procedure

Under inert atmosphere 8.4 g (150 mmol) of potassium hydroxide is dissolved in 150 ml of ethanol. After adding 10.0 g (31 mmol) of 2-bromo-1-(4-hydroxy-3,5-di-tert-butylphenyl)-ethanone in portions at room temperature stirring is continued for 16 hours. Then the reaction mixture is acidified with 10% HCl and extracted with ethylacetate. The collected organic phases are washed with water and brine, dried and evaporated. Crystallization of the crude product from hexane gives 3.8 g of compound 113, m.p. 73-75° C.

Workup

  1. extractionextracted with ethylacetate
  2. washThe collected organic phases are washed with water and brine
  3. customdried
  4. customevaporated
  5. customCrystallization of the crude product from hexane

Sources & evidence

ORD record
ord-fd8cb560517341caa04989e8aec8127b
Source dataset
uspto-grants-2010_10
Patent number
US07820865B2

Reaction notes

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