2-Aminophenol → N-[4-hydroxy-3,5-di-t-butyl-phenylacetyl]-2-hydroxyaniline

HRID 842126Notes

Reaction equation

HRID 842126 reaction equation
[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]([CH2:12][C:13](O)=[O:14])=[CH:4][C:3]=1[C:16]([CH3:19])([CH3:18])[CH3:17].[OH:20][C:21]1[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=1[NH2:23].C(N1C=CN=C1)(N1C=CN=C1)=O>>[OH:1][C:2]1[C:7]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:6][C:5]([CH2:12][C:13]([NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=2[OH:20])=[O:14])=[CH:4][C:3]=1[C:16]([CH3:17])([CH3:19])[CH3:18]

Participants

4

Reactant 3

HCID 58012-AminophenolHCID 682631,1'-CarbonyldiimidazoleHCID 27751103,5-Bis(1,1-dimethylethyl)-4-hydroxybenzeneacetic acid

Product 1

HCID 22618275N-[4-hydroxy-3,5-di-t-butyl-phenylacetyl]-2-hydroxyanilineYield 86.2%

Procedure

Using previously described procedures with 4-hydroxy-3,5-di-t-butyl-phenylacetic acid (45 g, 0.17 mol), 2-hydroxyaniline (20.7 g, 0.19 mol) and 1,1′-carbonyl diimidazole (29 g, 0.18 mol) the title compound (52.1 g, 86%) was obtained as a tan solid.

Sources & evidence

ORD record
ord-10e98025bd784214b312c85de6e6e20b
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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