O-Xylene → N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-4-methylhexahydrophthalimide

HRID 974357

Reaction equation

HRID 974357 reaction equation
[CH3:1][CH:2]1[CH2:12][CH2:11][CH:5]2[C:6]([O:8][C:9](=[O:10])[CH:4]2[CH2:3]1)=O.[C:13]([C:17]1[CH:18]=[C:19]([CH2:28][CH2:29][C:30]([NH:32][NH2:33])=[O:31])[CH:20]=[C:21]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:22]=1[OH:23])([CH3:16])([CH3:15])[CH3:14].C1(C)C(C)=CC=CC=1>O>[C:24]([C:21]1[CH:20]=[C:19]([CH2:28][CH2:29][C:30]([NH:32][N:33]2[C:9](=[O:10])[CH:4]3[CH2:3][CH:2]([CH3:1])[CH2:12][CH2:11][CH:5]3[C:6]2=[O:8])=[O:31])[CH:18]=[C:17]([C:13]([CH3:14])([CH3:15])[CH3:16])[C:22]=1[OH:23])([CH3:25])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 648653,5-Di-tert-butyl-4-hydroxyhydrocinnamic acid hydrazideHCID 86876Hexahydro-4-methylphthalic anhydride

Product 1

HCID 19902401N-[3-(3,5-di-t-butyl-4-hydroxyphenyl)propanamido]-4-methylhexahydrophthalimideYield 100.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-methylhexahydrophthalic anhydride (32.8 g, 200 mmol), 3-(3,5-di-t-butyl-4-hydroxyphenyl)propanoic acid hydrazide (58.4 g, 200 mmol) and 650 ml of xylene was refluxed for 90 minutes under a nitrogen atmosphere with the azeotropic removal of water. The solvent was removed on a rotary evaporator to afford approximately 89 g of a white solid having a melting range of 87°-92° C.

Workup

  1. customThe solvent was removed on a rotary evaporator

Sources & evidence

ORD record
ord-a07343b029b64fe6bbdc278a4e0cf9f4
Source dataset
uspto-grants-1991_11
Patent number
US05068356

Linked notes

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