Dimethylformamide → 2-Hydroxy-3,5-di-t-amylbenzoic acid

HRID 1580316Notes

Reaction equation

HRID 1580316 reaction equation
[C:1]([C:6]1[CH:11]=[C:10]([C:12]([CH2:15][CH3:16])([CH3:14])[CH3:13])[CH:9]=[CH:8][C:7]=1[OH:17])([CH2:4][CH3:5])([CH3:3])[CH3:2].[OH-:18].[K+].CN(C)[CH:22]=[O:23]>C1(C)C=CC=CC=1>[OH:17][C:7]1[C:6]([C:1]([CH2:4][CH3:5])([CH3:3])[CH3:2])=[CH:11][C:10]([C:12]([CH2:15][CH3:16])([CH3:14])[CH3:13])=[CH:9][C:8]=1[C:22]([OH:23])=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 84552,4-Di-tert-pentylphenolHCID 14797Potassium Hydroxide

Product 1

HCID 196022852-Hydroxy-3,5-di-t-amylbenzoic acidYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,4-di-t-amyl phenol (0.44 m) and KOH (0.5 m) were refluxed in toluene for two hours. Dimethylformamide (100 ml) was added and solvent was removed by distillation until the temperature reached 145°. CO2 was bubbled in and more solvent was removed until the temperature reached 160°. This temperature was maintained for four hours with CO2 passing in and the reaction mixture was worked up to give 2-hydroxy-3,5-di-t-amylbenzoic acid which was esterified to form the methyl ester, which had a boiling point of 127°-129°C at 0.7 mm Hg pressure, in 50% yield. The ester was then converted to the hydrazide by refluxing with hydrazine hydrate in aqueous ethanol. The hydrazide had a melting point of 132°-133°C and the following elemental analysis by weight:

Workup

  1. customsolvent was removed by distillation until the temperature
  2. customreached 145°
  3. customCO2 was bubbled in and more solvent
  4. customwas removed until the temperature
  5. customreached 160°
  6. temperatureThis temperature was maintained for four hours with CO2 passing in and the reaction mixture

Sources & evidence

ORD record
ord-1f33eef9882d45328b66bca0c03e90a7
Source dataset
uspto-grants-1976_01
Patent number
US03932505

Reaction notes

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