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

HRID 260372
Notes
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Reaction equation

HRID 260372 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6328Methyl iodideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-333168d5e6b9445094b42af73080bd3c
Source dataset
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05527824

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes