Acetic Acid → HCID 54320304, compound

HRID 435843Notes

Reaction equation

HRID 435843 reaction equation
[C:1]([C:5]1[C:6]([OH:32])=[C:7]([CH:15]([C:17]2[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:18]=2[OH:31])Br)[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)C>C(O)C>[C:1]([C:5]1[C:6](=[O:32])[C:7](=[CH:15][C:17]2[CH:22]=[C:21]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:20]=[C:19]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:18]=2[OH:31])[CH:8]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 540771882,2'-(Bromomethylene)bis(4,6-di-tert-butylphenol)

Product 1

HCID 54320304HCID 54320304, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Three tenths of a part of the di-(3,5-di-tert-butyl-2-hydroxyphenyl) bromomethane produced above is dissolved in 20 parts of ethanol and placed in the reaction vessel just above described. One part of 5 percent aqueous sodium hydroxide solution is added and a slow current of nitrogen is passed through the solution for 20 minutes. The reaction mixture is poured into a vessel containing crushed ice, neutralized with acetic acid and extracted with ether. The ether is evaporated and the residue crystallized twice from aqueous ethanol to yield (3,5-di-tert-butyl-2-oxo-3,5-cyclohexadien-1-ylidene)-(3,5-di-tert-butyl-2-hydroxyphenyl) methane.

Workup

  1. additionThe reaction mixture is poured into a vessel
  2. additioncontaining
  3. customcrushed ice
  4. extractionextracted with ether
  5. customThe ether is evaporated
  6. customthe residue crystallized twice from aqueous ethanol

Sources & evidence

ORD record
ord-40b22aaafa6a41d7b68bd90699fa7fb2
Source dataset
uspto-grants-1977_02
Patent number
US04006252

Reaction notes

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