Nitric Acid → 4-tert-Butyl-2,6-dinitrophenol

HRID 1956024Notes

Reaction equation

HRID 1956024 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.C(C1C=CC([OH:32])=CC=1)(C)(C)C.[N+]([O-])(O)=O>C(O)(=O)C>[N+:19]([C:7]1[CH:8]=[C:9]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:10]=[C:11]([N+:12]([O-:14])=[O:13])[C:6]=1[OH:32])([O-:21])=[O:20]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 73934-tert-Butylphenol2×HCID 36565Butralin

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The synthesis of N-sec-butyl-4-tert-butyl-2,6-dinitroaniline is generally described in a number of U.S. patents including, for example, U.S. Pat. Nos. 3,672,866; 3,927,127 and 3,991,116 all to Damiano. The process described in U.S. Pat. Nos. 3,672,866 and 3,991,116 begins with a starting material, 4-tert-butylphenol. The 4-tert-butylphenol is subjected to nitration utilizing nitric acid in acetic acid solution to produce 2,6-dinitro-4-tert-butylphenol. The 2,6-dinitro-4-tert-butylphenol is then chlorinated to produce 2,6-dinitro-4-tert-butylchlorobenzene. This 2,6-dinitro-4-tert-butylchlorobenzene is then converted into N-sec-butyl-4-tert-butyl-2,6-dinitroaniline by amination with sec-butylamine.

Sources & evidence

ORD record
ord-69fdc7da4830430e935378b9a9476884
Source dataset
uspto-grants-1998_07
Patent number
US05777168

Reaction notes

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