Acetic Acid → 4-Methylthio-3-nitrobenzoic acid

HRID 467334Notes

Reaction equation

HRID 467334 reaction equation
[CH3:1][S:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9]C)=[O:8])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14].[OH-].[Na+].C(O)(=O)C>C(O)C.O>[CH3:1][S:2][C:3]1[CH:12]=[CH:11][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[N+:13]([O-:15])=[O:14]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 21187831Methyl 4-(methylsulfanyl)-3-nitrobenzenecarboxylate

Product 1

HCID 5425314-Methylthio-3-nitrobenzoic acidYield 93.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 4-methylthio-3-nitrobenzoate (11.7 g) and sodium hydroxide (4.1 g) in ethanol (234 ml) and water (117 ml) was heated at reflux for 2 hours and was then concentrated in vacuo to about 70 ml. Water (250 ml) was added and the mixture was warmed to give a solution which was acidified with acetic acid (30 ml). The mixture was stirred while cooling and the resulting solid collected and washed with water to yield 4-methylthio-3-nitrobenzoic acid (10.3 g), m.p. 245°-247° C. [Elemental analysis: C,45.2; H,3.22; N,6.48; S,14.1%; calculated: C,45.07; H,3.29; N,6.57; S,15.02%].

Workup

  1. temperatureat reflux for 2 hours
  2. concentrationwas then concentrated in vacuo to about 70 ml
  3. additionWater (250 ml) was added
  4. temperaturethe mixture was warmed
  5. customto give a solution which
  6. temperaturewhile cooling
  7. customthe resulting solid collected
  8. washwashed with water

Sources & evidence

ORD record
ord-70b8ba8316fe4998be7e4b78283c050c
Source dataset
uspto-grants-1992_10
Patent number
US05159114

Reaction notes

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