4-Amino-2,6-di-tert-butylphenol → HCID 15044874, compound

HRID 728563Notes

Reaction equation

HRID 728563 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>C(OCC)C>[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

4

Reactant 2

HCID 3142204-Amino-2,6-di-tert-butylphenolHCID 641660Hexahydrophthalic anhydride, cis-

Product 1

HCID 15044874HCID 15044874, compoundYield 71.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution containing 5.68 g (0.03 mole) of 4-amino-2,6-di-t-butylphenol in 200 ml of diethyl ether was added dropwise to a solution of 4.62 g (0.03 mole) of cis-1,2-cyclohexanedicarboxylic anhydride in 200 ml of diethyl ether. 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 8.1 g of a solid. This material was recrystallized from a mixture of ethyl acetate and hexane to give 7.3 g of white solid 2-[N-(3,5-di-t-butyl-4-hydroxyphenyl)carbamoyl]-cis-cyclohexanecarboxylic acid, m.p. 181°-184° C. Analysis: Calculated for C22H33NO4 : %C, 70.4, %H, 8.9; %N, 3.7; Found: %C, 70.1; %H, 8.7; %N, 3.6.

Workup

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

Sources & evidence

ORD record
ord-7ce1b7e80e6c4e5f940a18ec7c8124dd
Source dataset
uspto-grants-1991_09
Patent number
US05049572

Reaction notes

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