Phenol → HCID 86733560, compound

HRID 1658338Notes

Reaction equation

HRID 1658338 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7](=O)[C:8]([O:10][CH2:11][CH3:12])=[O:9].S(=O)(=O)(O)O.[C:19]1([OH:25])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O>[OH:25][C:19]1[CH:24]=[CH:23][C:22]([C:7]([C:22]2[CH:23]=[CH:24][C:19]([OH:25])=[CH:20][CH:21]=2)([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 996PhenolHCID 1118Sulfuric Acid2×HCID 9989820Ethyl 2-pyridineglyoxylate

Product 1

HCID 86733560HCID 86733560, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g. Ethyl 2-pyridine-glyoxylate were cautiously added dropwise to a pre-cooled mixture of 100 ml. 85% sulphuric acid and 100 g. phenol, while stirring. The reaction mixture was externally cooled with water and ice to keep it at ambient temperature and to control the exothermic reaction. After stirring for 60 hours, the reaction mixture was poured into ice-water and washed with chloroform. The gum-like precipitate which separated and the aqueous phase were rendered alkaline with ammonium hydroxide and the resulting solution was treated with activated charcoal. After filtration, the solution obtained was adjusted to about pH 7 with diluted sulphuric acid to give a high yield of a crystalline precipitate of ethyl α, α-di(4-hydroxyphenyl)-2-pyridine-acetate. After crystallisation from isopropanol or ethyl acetate, the product was obtained in the form of a colourless, crystalline solid which melted, with decomposition, at 252° - 254°C.

Workup

  1. customat ambient temperature
  2. customthe exothermic reaction
  3. washwashed with chloroform
  4. customThe gum-like precipitate which separated
  5. additionthe resulting solution was treated with activated charcoal
  6. filtrationAfter filtration
  7. customthe solution obtained

Sources & evidence

ORD record
ord-48f7d8f5fe834a4695f6b6bfd81b061c
Source dataset
uspto-grants-1976_06
Patent number
US03963732

Reaction notes

Loading…