2-Nitrophenol → HCID 23370124, compound

HRID 1901065Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[C:11]([C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:23]=1[OH:24])[C:18](O)=[O:19])([CH3:14])([CH3:13])[CH3:12].FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])O.[Na+]>>[C:25]([C:22]1[CH:21]=[C:17]([CH:16]=[C:15]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:23]=1[OH:24])[C:18]([O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])=[O:19])([CH3:28])([CH3:27])[CH3:26]

Participants

Reactant 4

HCID 69472-Nitrophenol

HCID 9845Trifluoroacetic anhydride

HCID 150073,5-Di-tert-butyl-4-hydroxybenzoic acid

HCID 516892Sodium Bicarbonate

Product 1

HCID 23370124HCID 23370124, compoundYield 70.1%

Procedure

A mixture of o-nitrophenol (1.39 g), 3,5-di-t-butyl-4-hydroxybenzoic acid (2.50 g) and trifluoroacetic anhydride (8.5 ml) was stirred at room temperature overnight. The mixture was poured into ice water, neutralized with sodium hydrogen carbonate, extracted with ethyl acetate, washed with water, saturated saline, and dried over anhydrous MgSO4. The solvent was distilled off and crystallization of the residue from diisopropyl ether afforded 2-nitrophenyl 3,5-di-t-butyl-4-hydroxybenzoate (2.60 g, 70%).

Workup

extractionextracted with ethyl acetate
washwashed with water, saturated saline
dry with materialdried over anhydrous MgSO4
distillationThe solvent was distilled off
customcrystallization of the residue from diisopropyl ether

Sources & evidence

ORD record: ord-1a2e36b6d64c4ef39bf9996a14f8f160
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05576335

Reaction notes

Loading…