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

HRID 1956032Notes

Reaction equation

HRID 1956032 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[CH:7]=[CH:6][C:5]=1[O:14][CH3:15])([O-:3])=[O:2].[N+:16]([O-])([OH:18])=[O:17].S(=O)(=O)(O)O>C(Cl)CCl>[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([CH3:12])([CH3:11])[CH3:13])[CH:7]=[C:6]([N+:16]([O-:18])=[O:17])[C:5]=1[O:14][CH3:15])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 1118Sulfuric AcidHCID 41784474-Tert-butyl-1-methoxy-2-nitrobenzene3×

Product 1

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

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
50 °C

Procedure

The recovered 2-nitro-4-tertbutylanisole is then again subjected to nitration. Specifically, the 2-nitro-4-tertbutylanisole intermediate is mixed with between 2-9 parts (by volume) organic solvent such as ethylene dichloride. Next is the cooling of the reaction mixture of 2-nitro-4-tertbutylanisole and organic solvent in an ice-water bath to a temperature below 5° C. This is followed by the adding of a mixture of 70% nitric acid and 98% sulfuric acid while maintaining a temperature below 10° C. Following the acid mixture addition, the cooling bath is removed and the temperature of the reaction mixture is increased to 50° C. and maintained there for 2-10 hours to produce 2,6-dinitro-4-tertbutylanisole and a 2,4-dinitrophenol byproduct.

Workup

  1. temperaturewhile maintaining a temperature below 10° C
  2. additionthe acid mixture addition
  3. customthe cooling bath is removed
  4. temperaturemaintained there for 2-10 hours

Sources & evidence

ORD record
ord-89e60297595a4b0aa0e5980726685be8
Source dataset
uspto-grants-1998_07
Patent number
US05777168

Reaction notes

Loading…