Sodium Hydroxide → 2-(3-Methoxyphenylthiomethyl)-6-nitrobenzoic acid

HRID 322236Notes

Reaction equation

HRID 322236 reaction equation
[OH-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([S:11][CH2:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:14]=2[C:15]([O:17]C)=[O:16])[CH:8]=[CH:9][CH:10]=1>CO>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([S:11][CH2:12][C:13]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:14]=2[C:15]([OH:17])=[O:16])[CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22009996Methyl 2-(3-methoxyphenylthiomethyl)-6-nitrobenzoate

Product 1

HCID 177896322-(3-Methoxyphenylthiomethyl)-6-nitrobenzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In methanol (10 ml) was dissolved methyl 2-(3-methoxyphenylthiomethyl)-6-nitrobenzoate obtained in Reference Example 16 (0.96 g, 2.88 mmol), and a 4 mol/l aqueous solution of sodium hydroxide (10 ml) was added thereto, followed by heating under reflux for 2 hours. After the reaction, the reaction mixture was concentrated and adjusted to pH 3 with a 1 mol/l aqueous solution of hydrochloric acid to give 2-(3-methoxyphenylthiomethyl)-6-nitrobenzoic acid as a precipitated white solid (0.85 g, 92%).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 2 hours
  3. customAfter the reaction
  4. concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record
ord-a62b797a32ba4873b739d5eda1601ab6
Source dataset
uspto-grants-2001_04
Patent number
US06211227B1

Reaction notes

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