Water → 4-(3,5-di-tertiary-butyl-4-hydroxy-N-methylanilino)benzoic acid
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]Participants
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
- customthe resulting solid was collected
- filtrationThe chloroform solution was filtered
- washwashed with water
- dry with materialdried with magnesium sulfate
- customevaporated
- customto give a tan solid
- customThis material was recrystallized first from benzene
- additionfrom a mixture of ethanol and water
Sources & evidence
- ORD record
- ord-d83919df79ae49428e028e607b0070c2
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05416113
Reaction notes
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