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

HRID 2225205Notes

Reaction equation

HRID 2225205 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-d5814394b779410f801917aba81bf5c6
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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