Benzoic acid, 2,6-dinitro- → Methyl 2,6-dinitrobenzoate

HRID 1076987

Reaction equation

HRID 1076987 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=1[C:6]([OH:8])=[O:7])([O-:3])=[O:2].[CH3:16]N1C=CCN(C2C=CC(C)=CC=2)N1>CCOCC>[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=1[C:6]([O:8][CH3:16])=[O:7])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 119206Benzoic acid, 2,6-dinitro-HCID 202618531-Methyl-3-p-tolyltriazine

Product 1

HCID 333850Methyl 2,6-dinitrobenzoateYield 37.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2,6-Dinitrobenzoic acid (10.6 grams) is suspended in ether (125 ml.) at 0°C. 1-Methyl-3-p-tolyltriazine (8.2 grams) in ether (75 ml.) is added dropwise to the stirred reaction mixture in an ice bath. The reaction mixture is stirred at 0° for 1 hour and at room temperature for 1 hour. The reaction mixture is diluted to 1 l. with ether and the insoluble product collected by filtration. Recrystallization from methanol gives colorless crystals (3.65 grams, melting point 150°-151.5°). An additional 4.1 grams of product are obtained from the filtrate.

Workup

  1. additionThe reaction mixture is diluted to 1 l
  2. filtrationwith ether and the insoluble product collected by filtration
  3. customRecrystallization from methanol

Sources & evidence

ORD record
ord-49f47bae1e5e4f5d8346bbff5a856aec
Source dataset
uspto-grants-1976_05
Patent number
US03959289

Linked notes

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