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

HRID 1580316ノート

反応式

HRID 1580316 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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:

後処理

  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

出典と根拠

ORDレコード
ord-1f33eef9882d45328b66bca0c03e90a7
出典データセット
uspto-grants-1976_01
特許番号
US03932505

反応ノート

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