Nitric Acid → 4-Ethyl-2-methoxy-6-nitrophenol

HRID 325745

Reaction equation

HRID 325745 reaction equation
[N+:1]([O-:4])(O)=[O:2].[CH2:5]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([O:14][CH3:15])[CH:8]=1)[CH3:6]>C(O)(=O)C.ClCCl>[CH2:5]([C:7]1[CH:12]=[C:11]([N+:1]([O-:4])=[O:2])[C:10]([OH:13])=[C:9]([O:14][CH3:15])[CH:8]=1)[CH3:6]

Participants

5

Reactant 2

HCID 944Nitric AcidHCID 624654-Ethylguaiacol

Product 1

HCID 135962234-Ethyl-2-methoxy-6-nitrophenol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of fuming nitric acid (12.1 ml; s.g. 1.5) in glacial acetic acid (120 ml) was added in one portion to a stirred solution of 4-ethyl-2-methoxyphenol (41.7 g) in dry dichloromethane (800 ml). After 1 minute the solution was washed with water (3×300 ml), and the organic layer was dried over anhydrous sodium sulphate and evaporated in vacuo to give an orange crystalline residue. This was recrystallised from a mixture of methanol and water to give 4-ethyl-2-methoxy-6-nitrophenol (31.3 g), m.p. 59°-61° C.

Workup

  1. washAfter 1 minute the solution was washed with water (3×300 ml)
  2. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  3. customevaporated in vacuo
  4. customto give an orange crystalline residue
  5. customThis was recrystallised from a mixture of methanol and water

Sources & evidence

ORD record
ord-f62c0765f89d475eae04093d8b508a96
Source dataset
uspto-grants-1984_04
Patent number
US04442115

Linked notes

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