Hydrochloric Acid → 2-(3-Methylthiophen-2-YL)acetic acid
Reaction equation
O.NN.C[O:5][C:6](=[O:15])[C:7]([C:9]1[S:10][CH:11]=[CH:12][C:13]=1[CH3:14])=O.[OH-].[K+].Cl>C(O)COCCO.O>[CH3:14][C:13]1[CH:12]=[CH:11][S:10][C:9]=1[CH2:7][C:6]([OH:15])=[O:5]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 3040 °C
Procedure
112.5 ml (116 g, 2.312 mol) of hydrazine hydrate were added slowly to a solution of 90 g (0.489 mol) of methyl(3-methylthiophen-2-yl)oxoacetate in 260 ml of diethylene glycol, and the mixture was heated under reflux for 30 min. After cooling to 3040° C., 82 g (1.246 mol) of potassium hydroxide were added a little at a time, which was accompanied by a temperature increase to 70-80° C. with simultaneous evolution of nitrogen. The mixture was then slowly heated to reflux and stirred at this temperature for a total of 5 h. After cooling to room temperature, the mixture was poured into 2 l of water, adjusted to pH=1 using 250 ml of semi-concentrated hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over magnesium sulphate and filtered off and the solvent was removed, which gave 50 g of (3-methylthiophen-2-yl)acetic acid. Yield: 66%. 1H-NMR (DMSO): δ=7.25 (d, 1H), 6.84 (d, 2H), 3.67 (s, 2H), 2.11 (s, 3H).
Workup
- temperaturethe mixture was heated
- temperatureunder reflux for 30 min
- temperatureincrease to 70-80° C. with simultaneous evolution of nitrogen
- temperatureThe mixture was then slowly heated
- temperatureto reflux
- temperatureAfter cooling to room temperature
- extractionextracted with ethyl acetate
- dry with materialThe organic phase was dried over magnesium sulphate
- filtrationfiltered off
- customthe solvent was removed
Sources & evidence
- ORD record
- ord-17e47cb4cd8e4328a90372266f4156fb
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07629294B2
Reaction notes
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