Lithium Hydroxide → (4-Methoxymethylsulfanyl-phenyl)-acetic acid

HRID 398657Notes

Reaction equation

HRID 398657 reaction equation
C[O:2][C:3](=[O:15])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][O:13][CH3:14])=[CH:7][CH:6]=1.O1CCCC1.[OH-].[Li+]>CO.O>[CH3:14][O:13][CH2:12][S:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:15])=[O:2])=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 67483162(4-Methoxymethylsulfanyl-phenyl)-acetic acid methyl ester

Product 1

HCID 21094076(4-Methoxymethylsulfanyl-phenyl)-acetic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (4-methoxymethylsulfanyl-phenyl)-acetic acid methyl ester (441 mg, 1.90 mmol) in methanol (1 mL), water (0.5 mL), and tetrahydrofuran (0.5 mL) was treated with lithium hydroxide (51 mg, 2.1 mmol). The reaction mixture was stirred at 25° C. for 20 h. At this time, the reaction was concentrated in vacuo. The residue was re-dissolved in water and extracted with ethyl acetate. The aqueous layer was then acidified to pH=1 with a 1N aqueous hydrochloric acid solution. This solution was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered, and concentrated in vacuo to afford (4-methoxymethylsulfanyl-phenyl)-acetic acid (402 mg, 100%) as a clear oil which was used without further purification.

Workup

  1. concentrationAt this time, the reaction was concentrated in vacuo
  2. dissolutionThe residue was re-dissolved in water
  3. extractionextracted with ethyl acetate
  4. extractionThis solution was extracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a909c214124048d29b9fdcf71786e40b
Source dataset
uspto-grants-2003_08
Patent number
US06610846B1

Reaction notes

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