Hydrochloric Acid → 5-Hydroxy-4-methoxy-2-nitrobenzoic acid

HRID 631203Notes

Reaction equation

HRID 631203 reaction equation
[CH3:1][O:2][C:3]1[C:11]([O:12]C)=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1.Cl>[OH-].[K+]>[OH:12][C:11]1[C:3]([O:2][CH3:1])=[CH:4][C:5]([N+:14]([O-:16])=[O:15])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 786904,5-Dimethoxy-2-nitrobenzoic acid

Product 1

HCID 139156695-Hydroxy-4-methoxy-2-nitrobenzoic acidYield 95.1%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4,5-dimethoxy-2-nitrobenzoic acid (20.6 g, 90.7 mmol) in 20% KOH solution (136 mL) was heated at 100° C. for 12 hours. After it was cooled with ice, it was acidified with concentrated HCl to pH 2. It was filtered, washed with CH2Cl2 and EtOAc, and dried over vacuum to afford 5-hydroxy-4-methoxy-2-nitrobenzoic acid as solid (18.38 g, 95%). 1H NMR (300 MHz, DMSO-d6) δ 7.29 (s, 1H), 6.90 (s, 1H), 4.8 (br, 1H), 3.77 (s, 3H).

Workup

  1. temperatureAfter it was cooled with ice, it
  2. filtrationIt was filtered
  3. washwashed with CH2Cl2 and EtOAc
  4. customdried over vacuum

Sources & evidence

ORD record
ord-5c40ddaf9c36414ab3d755c5714895a9
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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