Toluene → HCID 15044873, compound

HRID 728562Notes

Reaction equation

HRID 728562 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:17]1(=[O:27])[O:22][C:20](=[O:21])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.C1(C)C=CC=CC=1>C(OCC)C>[C:8]([C:6]1[CH:7]=[C:2]([NH:1][C:17]([C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20]([OH:22])=[O:21])=[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

5

Reactant 3

HCID 1140TolueneHCID 6811Phthalic AnhydrideHCID 3142204-Amino-2,6-di-tert-butylphenol

Product 1

HCID 15044873HCID 15044873, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 5.60 g (0.03 mole) of the known compound 4-amino-2,6-di-t-butylphenol in 100 ml of diethyl ether was added dropwise over a period of twenty minutes to a solution of 4.44 g (0.03 mole) of phthalic anhydride in 200 ml of a 1:2 mixture of diethyl ether:toluene. The reaction mixture was stirred at room temperature for about sixteen hours. The resulting precipitate was collected, rinsed with a mixture of diethyl ether and hexane, and dried to give 6.8 g of a white solid. This material was recrystallized from a mixture of ethyl acetate and hexane to give 5.9 g of white solid 2-[N-(3,5-di-t-butyl-4-hydroxyphenyl)carbamoyl]benzoic acid, m.p. 191°-192° C. Analysis: Calculated for C22H27NO4 : %C, 71.5; %H, 7.4, %N, 3.8; Found: %C, 71.8; %H, 7.3; %N, 3.7.

Workup

  1. customThe resulting precipitate was collected
  2. washrinsed with a mixture of diethyl ether and hexane
  3. customdried

Sources & evidence

ORD record
ord-5dcae065190548b8adbf4f95d883c5e1
Source dataset
uspto-grants-1991_09
Patent number
US05049572

Reaction notes

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