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

HRID 973270Notes

Reaction equation

HRID 973270 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-57f09f5a251f4f85bed66226c34e7d8f
Source dataset
uspto-grants-1977_10
Patent number
US04055654

Reaction notes

Loading…