Methanol → Methyl 5-chloro-2-nitrobenzoate

HRID 128477

Reaction equation

HRID 128477 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:14]O>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([O:9][CH3:14])=[O:8]

Participants

3

Reactant 2

HCID 887MethanolHCID 172865-Chloro-2-nitrobenzoic acid

Product 1

HCID 171018Methyl 5-chloro-2-nitrobenzoate

Procedure

5-Chloro-2-nitrobenzoic acid (20.1 g,; 0.10 mol), is dissolved in anhydrous methanol (100 ml) and anhydrous hydrogen chloride gas is bubbled into the reaction mixture for 4 hours at room temperature. The reaction mixture is then poured into water and the aqueous mixture triturated with hexane, the hexane layer decanted, dried (anhd. MgSO4) and the solvent removed under vacuum to afford 11.7 g of methyl 5-chloro-2-nitrobenzoate, mp 50°-51° C.

Workup

  1. customanhydrous hydrogen chloride gas is bubbled into the reaction mixture for 4 hours at room temperature
  2. additionThe reaction mixture is then poured into water
  3. customthe aqueous mixture triturated with hexane
  4. customthe hexane layer decanted
  5. dry with materialdried (anhd. MgSO4)
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-c210b6f1d1844ee9889f11ccfe0a161c
Source dataset
uspto-grants-1981_03
Patent number
US04259510

Linked notes

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