Sodium Hydroxide → 5-Amino-2,4-dimethylbenzoic acid

HRID 541223Notes

Reaction equation

HRID 541223 reaction equation
[NH2:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>CO.O>[NH2:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 46835529Methyl 5-amino-2,4-dimethylbenzoate

Product 1

HCID 5966895-Amino-2,4-dimethylbenzoic acidYield 90.4%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
50 °C

Procedure

A mixture of methyl 5-amino-2,4-dimethylbenzoate (1.2 g, 6.70 mmol, 1.00 equiv) and sodium hydroxide (1.5 g, 37.50 mmol, 5.60 equiv) in methanol/H2O (20/20 mL) was stirred overnight at 50° C. After cooling to ambient temperature, the organic phase was removed under reduced pressure. The pH of the remaining aqueous layer was adjusted to ˜4-5 with hydrogen chloride (aq., 2 M). The resulting solids were collected by filtration and dried to yield 1.0 g of a yellow solid.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. customthe organic phase was removed under reduced pressure
  3. filtrationThe resulting solids were collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-0fa06acd826542529e735f1df7c041ce
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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