Glyoxylic Acid → Terbuficin

HRID 436192Notes

Reaction equation

HRID 436192 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[OH:15])([CH3:4])([CH3:3])[CH3:2].[C:16]([OH:20])(=[O:19])[CH:17]=O.[OH2:21]>C(Cl)(Cl)(Cl)Cl.Cl>[OH:15][C:6]1[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:10][C:9]([CH:17]([C:9]2[CH:10]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:6]([OH:21])=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=2)[C:16]([OH:20])=[O:19])=[CH:8][C:7]=1[C:11]([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 760Glyoxylic AcidHCID 962WaterHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 3084235Terbuficin

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolvent2×HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
50 °C

Procedure

103 g of 2,6-di-tert.-butyl-phenol (0.5 mol) and 21 g of glyoxylic acid (0.25 mol) of (CHO.COOH) . 1/2 H2O) were dissolved in 300 ml of carbon tetrachloride and stirred at 50° C for about 40 hours. During the first 6 hours, a weak hydrogen chloride stream was passed through the solution, later saturation was completed from time to time by feeding in hydrogen chloride. After condensation was complete, the solvent was eliminated. The product obtained in a pasty form was dissolved and precipitated several times from hexane. The crystallized compound having a faint yellowish tinge melted at 211° C.

Workup

  1. customDuring the first 6 hours
  2. customAfter condensation
  3. customThe product obtained in a pasty form
  4. dissolutionwas dissolved
  5. customprecipitated several times from hexane

Sources & evidence

ORD record
ord-34607cfc7e914cb09c42e026741d5972
Source dataset
uspto-grants-1977_02
Patent number
US04007282

Reaction notes

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