Phthalic Anhydride → HCID 15598813, compound

HRID 986041Notes

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:23]1(=[O:33])[O:28][C:26](=[O:27])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12>>[C:19]([C:10]1[CH:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:1][C:23]([C:24]3[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=3[C:26]([OH:28])=[O:27])=[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

Reactant 2

HCID 6811Phthalic Anhydride

HCID 155988104'-Amino-3,5-di-t-butyl-4-hydroxybiphenyl

Product 1

HCID 15598813HCID 15598813, compoundYield 53.9%

Procedure

To a solution of 2.97 g (0.01 mole) of 4'-amino-3,5-di-t-butyl-4-hydroxy biphenyl in 200 ml of diethyl ester was added a solution of 1.48 g (0.01 mole) of phthalic anhydride, and the resulting solution was stirred for about 16 hours. The solvents were removed under vacuum and the residual solid was recrystallized from a mixture of ethyl acetate and hexane to give 2.4 g of 2-{N-[4-(3,5-di-t-butyl-4-hydroxyphenyl)phenyl]carbamoyl} benzoic acid, m.p. 196°-198° C. Analysis: Calculated for C28H31NO4 ; % C, 75.5; % H, 7.0; % N, 3.1; Found: % C, 75.5; % H, 7.1; % N, 3.0.

Workup

customThe solvents were removed under vacuum
customthe residual solid was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record: ord-11ac1b4ee3e24c5897d997c99b131f0d
Source dataset: uspto-grants-1987_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04710515

Reaction notes

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