Methanol → Methyl 5-chloro-2-nitrobenzoate

HRID 444016Notes

Reaction equation

HRID 444016 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-ee64b6d87b40486397f846fa8914662e
Source dataset
uspto-grants-1981_04
Patent number
US04262152

Reaction notes

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