2-Nitrophenol → 4-tert-Butyl-2,6-dinitroanisole

HRID 1377010Notes

Reaction equation

C(N[C:6]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:8][C:7]=1[N+:19]([O-:21])=[O:20])(CC)C.[N+](C1C=CC=C[C:26]=1[OH:31])([O-])=O.[N+](C1C=C(C(C)(C)C)C=C([N+]([O-])=O)C=1O)([O-])=O.CI.C(=O)([O-])[O-].[K+].[K+]>>[C:15]([C:9]1[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]([O:31][CH3:26])=[C:7]([N+:19]([O-:21])=[O:20])[CH:8]=1)([CH3:18])([CH3:17])[CH3:16]

Participants

Reactant 4

HCID 69472-Nitrophenol2×

HCID 200424-tert-Butyl-2,6-dinitrophenol

HCID 36565Butralin

HCID 86747754Methyl iodide potassium carbonate

Product 1

HCID 42526024-tert-Butyl-2,6-dinitroanisole

Procedure

An alternative synthesis for N-sec-butyl-4-tert-butyl-2,6-dinitroaniline is set forth in U.S. Pat. Nos. 4,289,907 and 4,395,572 to Chan. The starting material in this synthesis is a nitrophenol such as 2,6-dinitro-4-tert-butylphenol. The nitrophenol is methylated by reaction with methyl iodide/potassium carbonate to produce 4-tert-butyl-2,6-dinitroanisole. The 4-tert-butyl-2,6-dinitroanisole is then reacted with sec-butylamine to produce N-sec-butyl-4-tert-butyl-2,6-dinitroaniline. While effective in producing the desired product, this process also suffers from a number of distinct disadvantages.

Sources & evidence

ORD record: ord-f92da87f7de34fbf9a06d53824d05a63
Source dataset: uspto-grants-1997_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05663441

Reaction notes

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