2,4-Di-tert-pentylphenol → 3-Nitro-4-(2,4-bis(1,1-dimethylpropyl)phenoxy)-pyridine

HRID 1656556Notes

Reaction equation

[CH3:1][C:2]([C:6]1[CH:11]=[C:10]([C:12]([CH3:16])([CH3:15])[CH2:13][CH3:14])[CH:9]=[CH:8][C:7]=1[OH:17])([CH3:5])[CH2:3][CH3:4].[H-].[Na+].Cl[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28]>O1CCCC1>[N+:27]([C:22]1[CH:23]=[N:24][CH:25]=[CH:26][C:21]=1[O:17][C:7]1[CH:8]=[CH:9][C:10]([C:12]([CH3:15])([CH3:16])[CH2:13][CH3:14])=[CH:11][C:6]=1[C:2]([CH3:1])([CH3:5])[CH2:3][CH3:4])([O-:29])=[O:28]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 2,4-bis(1,1-dimethylpropyl)phenol (9.23 g, 0.039 mol) in dry tetrahydrofuran (30 mL) was stirred at room temperature under nitrogen atmosphere. Sodium hydride (1.14 g of 80% dispersion, 0.04 mol) in dry tetrahydrofuran (10 mL) was added and the mixture stirred for 30 minutes to give a clear, green solution. 4-Chloro-3-nitropyridine (5.0 g, 0.032 mol) was added and the mixture heated to 50° C. for 4 hours. The mixture was cooled and submitted to aqueous, acidic work-up. The crude product was purified by chromatogaphy on silica gel with dichloromethane eluent to give the product 3-nitro-4-(2,4-bis(1,1-dimethylpropyl)phenoxy)-pyridine in 65% yield. Analyses by proton NMR and mass spectroscopy were consistent with the proposed structure.

Workup

customto give a clear, green solution
temperatureThe mixture was cooled
customThe crude product was purified by chromatogaphy on silica gel with dichloromethane eluent

Sources & evidence

ORD record: ord-444ab7e332594862a5483a84d4d1e462
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05254592

Reaction notes

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