Lithium Hydroxide → 3-(1,3-Thiazol-2-yl)benzoic acid

HRID 1374276Notes

Reaction equation

HRID 1374276 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([O:11]C)=[O:10].[OH-].[Li+]>C1COCC1.O>[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([CH:13]=[CH:14][CH:15]=1)[C:9]([OH:11])=[O:10]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 18945333Methyl 3-(1,3-thiazol-2-yl)benzoate

Product 1

HCID 210750873-(1,3-Thiazol-2-yl)benzoic acidYield 72.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Preparation H11, Step 4: A solution of 0.6 g (0.0027 mol) of methyl 3-(thiazol-2-yl)benzoate in 6 ml of THF and 1.2 ml of water was charged with 0.11 g (0.0046 mol) of lithium hydroxide. The reaction mixture was stirred at RT overnight. THF was removed and the aqueous layer was washed with ether and acidified with 1.5 N HCl. The solid product was extracted with ethyl acetate. The organic layer was washed with brine and concentrated to afford 3-(thiazol-2-yl)benzoic acid (0.4 g) as an off white solid obtained. 1H NMR (400 MHz, CDCl3): 7.45 (d, 1H), 7.63 (m, 1H), 8.0 (d, 1H), 8.22 (d, 1H), 8.30 (d, 1H), 8.79 (s, 1H). MS found: (M−H)−=204.

Workup

  1. customPreparation H11, Step 4
  2. customTHF was removed
  3. washthe aqueous layer was washed with ether
  4. extractionThe solid product was extracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-99a7580602e346c5b546760458785b0e
Source dataset
uspto-grants-2007_01
Patent number
US07163937B2

Reaction notes

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