Dimethyl Sulfate → p-tert-Butylanisole

HRID 1956027Notes

Reaction equation

[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].S(OC)(O[CH3:16])(=O)=O>>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([O:11][CH3:16])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 2

HCID 6497Dimethyl Sulfate

HCID 73934-tert-Butylphenol

Product 1

HCID 94750p-tert-Butylanisole

Procedure

More specifically, the process for producing N-sec-butyl-4-tert-butyl-2,6-dinitroaniline comprises reacting 4-tert-butylphenol with dimethyl sulfate to produce 4-tert-butylanisole. The 4-tert-butylanisole is then reacted with a nitrating agent including a mixture of nitric acid, sulfuric acid and oleum to produce 2,6-dinitro-4-tert-butylanisole. The 2,6-dinitro-4-tert-butylanisole is then reacted with sec-butylamine to produce N-sec-butyl-4-tert-butyl-2,6-dinitroaniline.

Sources & evidence

ORD record: ord-b7099e4ca00948a9b1c70f65ad697885
Source dataset: uspto-grants-1998_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05777168

Reaction notes

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