Lithium Hydroxide → 5-Hydroxyisophthalic acid

HRID 45740Notes

Reaction equation

HRID 45740 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:12]([O:14]C)=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Li+]>C1COCC1>[OH:1][C:2]1[CH:3]=[C:4]([C:12]([OH:14])=[O:13])[CH:5]=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 830651,3-Benzenedicarboxylic acid, 5-hydroxy-, 1,3-dimethyl ester

Product 1

HCID 692575-Hydroxyisophthalic acidYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To dimethyl 5-hydroxyisophthalate (4.0 g, 19.03 mmol, 1.00 equiv) in THF (10 mL) was added lithium hydroxide (20 mL, 2M in water) and the resulting solution was stirred overnight at 40° C. The mixture concentrated under vacuum to remove the organic solvents and then the pH of the solution was adjusted to ˜2 with 6N hydrochloric acid. The resulting solids were collected by filtration and dried in a vacuum oven to afford 2.0 g (58%) of 5-hydroxyisophthalic acid as a white solid.

Workup

  1. concentrationThe mixture concentrated under vacuum
  2. customto remove the organic solvents
  3. filtrationThe resulting solids were collected by filtration
  4. customdried in a vacuum oven

Sources & evidence

ORD record
ord-6caa6e20c67a41f6b1ca7271b7a871a0
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Reaction notes

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