4-Amino-2,6-di-tert-butylphenol → 2-[N-(3,5-Di-t-butyl-4-hydroxyphenyl)carbamoyl]-transcyclohexanecarboxylic Acid
Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:5]([OH:12])=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH:3]=1.[C@@H:17]12[C:26](=[O:27])[O:25][C:23](=[O:24])[C@H:18]1[CH2:19][CH2:20][CH2:21][CH2:22]2>COCCOC>[C:8]([C:6]1[CH:7]=[C:2]([NH:1][C:26]([C@@H:17]2[CH2:22][CH2:21][CH2:20][CH2:19][C@H:18]2[C:23]([OH:25])=[O:24])=[O:27])[CH:3]=[C:4]([C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]=1[OH:12])([CH3:9])([CH3:10])[CH3:11]Participants
Procedure
A solution containing 4.00 g (0.022 mole) of 4-amino-2,6-di-t-butylphenol in 50 ml of 1,2-dimethoxyethane was added dropwise over a period of ten minutes to a solution of 3.35 g (0.022 mole) of trans-1,2-cyclohexanedicarboxylic anhydride in 50 ml of 1,2-dimethoxyethane. The reaction mixture was stirred at room temperature for about seventy-two hours. The solvent was removed under vacuum and the residual solid was triturated with a mixture of diethyl ether and hexane. The resulting solid was recrystallized from a mixture of ethyl acetate and hexane to give 4.4 g of white solid 2-[N-(3,5-di-t-butyl-4-hydroxyphenyl) carbamoyl]-trans-cyclohexanecarboxylic acid, m.p. 247°-252° C. Analysis: Calculated for C22H33NO4 : %C, 70.4; %H, 8.9; %N, 3.7; Found: %C, 70.4; %H, 8.9; %N, 3.6.
Workup
- customThe solvent was removed under vacuum
- customthe residual solid was triturated with a mixture of diethyl ether and hexane
- customThe resulting solid was recrystallized from a mixture of ethyl acetate and hexane
Sources & evidence
- ORD record
- ord-0ab17728c17f49faa93e3c95ed0795de
- Source dataset
- uspto-grants-1991_09
- Patent number
- US05049572
Reaction notes
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