Hexahydrophthalic anhydride, cis- → HCID 54483369, compound

HRID 1085389Notes

Reaction equation

HRID 1085389 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:11]([OH:18])=[C:10]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:9]=2)=[CH:4][CH:3]=1.[C@@H:23]12[C:32](=[O:33])[O:31][C:29](=[O:30])[C@@H:24]1[CH2:25][CH2:26][CH2:27][CH2:28]2>C(OCC)C>[C:19]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:32]([C@H:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C@H:24]3[C:29]([OH:31])=[O:30])=[O:33])=[CH:3][CH:4]=2)[CH:13]=[C:12]([C:14]([CH3:15])([CH3:16])[CH3:17])[C:11]=1[OH:18])([CH3:22])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 641660Hexahydrophthalic anhydride, cis-HCID 155988104'-Amino-3,5-di-t-butyl-4-hydroxybiphenyl

Product 1

HCID 54483369HCID 54483369, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a solution of 2.97 g of 4'-amino-3,5-di-t-butyl-4-hydroxybiphenyl in 200 ml of diethyl ether was added a solution of 1.54 g (0.01 mole) of cis-1,2-cyclohexanedicarboxylic anhydride in 75 ml of diethyl ether, and the resulting solution was stirred for about 16 hours. A solid was removed by filtration, rinsed with diethyl ether and hexane and then recrystallized from a mixture of ethyl acetate and hexane to give 3.17 g of solid cis-2-{N-[4-(3,5-di-t-butyl-4-hydroxyphenyl)phenyl]carbamyl}-cyclohexanecarboxylic acid, m.p. 217°-220° C. Analysis: Calculated for C28H37NO4 : % C, 74.5; % H, 8.3; % N, 3.1; Found: % C, 74.6; % H, 8.3; % N, 3.0.

Workup

  1. customA solid was removed by filtration
  2. washrinsed with diethyl ether and hexane
  3. customrecrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-714d2947ec234b3a8bb34776a0c9b040
Source dataset
uspto-grants-1991_04
Patent number
USRE033574

Reaction notes

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