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Water → 4-(3,5-di-tertiary-butyl-4-hydroxy-N-methylanilino)benzoic acid

HRID 260372
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 260372
[C:1]([C:5]1[CH:6]=[C:7]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[NH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].O.[CH3:27]N(C)C=O>CI>[C:22]([C:19]1[CH:18]=[C:7]([CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:20]=1[OH:21])[N:8]([C:9]1[CH:10]=[CH:11][C:12]([C:13]([OH:15])=[O:14])=[CH:16][CH:17]=1)[CH3:27])([CH3:25])([CH3:24])[CH3:23]
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Komponenten

5

Edukt 3

HCID 962WaterHCID 6228DimethylformamideHCID 139604064-(3,5-Di-tertiary-butyl-4-hydroxyanilino)benzoic acid

Produkt 1

HCID 224015834-(3,5-di-tertiary-butyl-4-hydroxy-N-methylanilino)benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6328Methyl iodideLösungsmittel

Versuchsvorschrift

A solution of 3.4 g (0.010 mole) of 4-(3,5-di-tertiary-butyl-4-hydroxyanilino)benzoic acid (prepared in Example 1) in 35 ml of N,N-dimethylformamide and 3.5 ml of methyl iodide was heated at 95° C. for about 48 hours under nitrogen. The reaction mixture was poured into cold water and the resulting solid was collected and then taken up in chloroform. The chloroform solution was filtered, washed with water, dried with magnesium sulfate and evaporated to give a tan solid. This material was recrystallized first from benzene and then from a mixture of ethanol and water to give 1.5 g of white crystalline 4-(3,5-di-tertiary-butyl-4-hydroxy-N-methylanilino)benzoic acid, m.p. 240°-244° C. Analysis: Calculated for C22H29NO3 : % C, 74.3; % H, 8.2; % N, 3.9. Found: % C, 74.4; % H, 8.3; % N, 3.5.

Aufarbeitung

  1. customthe resulting solid was collected
  2. filtrationThe chloroform solution was filtered
  3. washwashed with water
  4. dry with materialdried with magnesium sulfate
  5. customevaporated
  6. customto give a tan solid
  7. customThis material was recrystallized first from benzene
  8. additionfrom a mixture of ethanol and water

Quellen und Nachweise

ORD-Eintrag
ord-333168d5e6b9445094b42af73080bd3c
Quelldatensatz
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05527824

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