Methanol → Benzoic acid, 3,4-dihydroxy-5-nitro-, methyl ester

HRID 1643816Notes

Reaction equation

HRID 1643816 reaction equation
S(Cl)(Cl)=O.[OH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1[OH:15])[C:9]([OH:11])=[O:10].[CH3:19]O>>[OH:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1[OH:15])[C:9]([O:11][CH3:19])=[O:10]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 144509823,4-Dihydroxy-5-nitrobenzoic acid

Product 1

HCID 5747973Benzoic acid, 3,4-dihydroxy-5-nitro-, methyl esterYield 71.4%

Procedure

Thionyl chloride (6.07 mL, 83 mmol) was added drop wise to a stirred solution of 3,4-dihydroxy-5-nitrobenzoic acid (14.4 g, 72.3 mmol) in MeOH (70 mL) at room temperature for 1 h. The reaction mixture was refluxed for 3 h and concentrated. The residue was recrystallized from water and vacuum-dried to afford the desired ester (11.0 g, 51.6 mmol, 71.4% yield).

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. concentrationconcentrated
  3. customThe residue was recrystallized from water
  4. customvacuum-dried

Sources & evidence

ORD record
ord-25a78bb0fc6845988cafdfc2477a68d2
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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