Lithium Hydroxide → 4-(Oxazol-2-yl)benzoic acid

HRID 14095

Reaction equation

HRID 14095 reaction equation
[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12]C)=[O:11])=[CH:8][CH:7]=1.[OH-].[Li+]>O1CCCC1.CO.O>[O:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[CH:8][C:9]([C:10]([OH:12])=[O:11])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 21985208Methyl 4-(oxazol-2-yl)benzoate

Product 1

HCID 210858714-(Oxazol-2-yl)benzoic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a stirred solution of methyl 4-(1,3-oxazol-2-yl)benzoate (690 mg, 3.4 mmol) in a mixture of 2:1:1 tetrahydrofuran/methanol/water (20 mL) is added lithium hydroxide (430 mg, 3 mmol). The reaction mixture is stirred at room temperature for 2 h. The solvent is removed under reduced pressure and the residue is partitioned between diethyl ether and water. The aqueous layer is acidified to pH 1 with 1 N hydrochloric acid and a precipitate is observed. The solid is collected by filtration to afford the title compound. 1H NMR (300 MHz, CD3OD) δ 8.14 (s, 4H), 8.05 (s, 1H), 7.36 (s, 1H).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customthe residue is partitioned between diethyl ether and water
  3. filtrationThe solid is collected by filtration

Sources & evidence

ORD record
ord-fb4424f91a924166aa16f184b86fa8ef
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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