1,3-Benzenedicarboxylic acid, 4-methyl-, 1,3-dimethyl ester → 4-Methylbenzene-1,3-dicarboxylic acid

HRID 265859

Reaction equation

HRID 265859 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10]C)=[O:9])=[CH:4][C:3]=1[C:12]([O:14]C)=[O:13].O[Li].O>C1COCC1.CO.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:10])=[O:9])=[CH:4][C:3]=1[C:12]([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 899711,3-Benzenedicarboxylic acid, 4-methyl-, 1,3-dimethyl esterHCID 168937Lithium hydroxide, monohydrate

Product 1

HCID 5957504-Methylbenzene-1,3-dicarboxylic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

A solution of 2-20 (1.5 g, 7.2 mmoles) in THF/MeOH/H2O (1:1:1) (36 ml) at room temperature was treated with LiOH.H2O (1.5 g, 36 mmoles). After stirring for 3 hours, the solvent was removed and the residue acidified with 1N HCl. This was extracted with EtOAc, and the extract was dried (MgSO4) and concentrated to give 2-21.

Workup

  1. customthe solvent was removed
  2. extractionThis was extracted with EtOAc
  3. dry with materialthe extract was dried (MgSO4)
  4. concentrationconcentrated
  5. customto give 2-21

Sources & evidence

ORD record
ord-a4daebdea2f44a1488ff83b844dfc640
Source dataset
uspto-grants-1997_07
Patent number
US05648368

Linked notes

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