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

HRID 871248Notes

Reaction equation

HRID 871248 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-d6f202fb8d2746d4a07ef2f9c6d60aa9
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

Loading…