2,4-Di-tert-butylphenol → HCID 86733274, compound

HRID 1606324Notes

Reaction equation

HRID 1606324 reaction equation
[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].C[O:17][C:18]([C:20]#[C:21][C:22]([O:24]C)=[O:23])=[O:19].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH-].[Na+]>CCOCC>[C:1]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:6]=1[O:15]/[C:20](=[CH:21]\[C:22]([OH:24])=[O:23])/[C:18]([OH:19])=[O:17])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 73112,4-Di-tert-butylphenolHCID 12980Dimethyl acetylenedicarboxylateHCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxide

Product 1

HCID 86733274HCID 86733274, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2060 parts of 2,4-di-t-butylphenol, 1040 parts by volume of acetylene dicarboxylic acid dimethyl ester and 10 parts of benzyltrimethylammonium hydroxide was heated on a steam bath until a rapid exothermic reaction had occurred. The mixture was cooled to room temperature and ether was added. The ether extract was washed with N sodium hydroxide solution, sodium chloride solution and water, then the ether was removed by evaporation. The residue obtained was refluxed for three hours with 5000 parts of 5N sodium hydroxide solution. After cooling the mixture to room temperature, the solid which precipitated was removed by filtration.

Workup

  1. temperaturewas heated on a steam bath until a rapid exothermic reaction
  2. extractionThe ether extract
  3. washwas washed with N sodium hydroxide solution, sodium chloride solution and water
  4. customthe ether was removed by evaporation
  5. customThe residue obtained
  6. temperatureAfter cooling the mixture to room temperature
  7. customthe solid which precipitated
  8. customwas removed by filtration

Sources & evidence

ORD record
ord-11881ba862a749a2a0f19a2cd2e7702d
Source dataset
uspto-grants-1976_04
Patent number
US03952104

Reaction notes

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