Potassium Hydroxide → [3-(4'-Chloro-4-methylbiphenyl-3-yl)-1,1-dimethylprop-2-ynyloxy]acetic acid
Reaction equation
[OH-].[K+].C[O:4][C:5](=[O:27])[CH2:6][O:7][C:8]([CH3:26])([CH3:25])[C:9]#[C:10][C:11]1[CH:12]=[C:13]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)[CH:14]=[CH:15][C:16]=1[CH3:17]>O1CCOCC1.O>[Cl:24][C:21]1[CH:20]=[CH:19][C:18]([C:13]2[CH:14]=[CH:15][C:16]([CH3:17])=[C:11]([C:10]#[C:9][C:8]([CH3:26])([CH3:25])[O:7][CH2:6][C:5]([OH:27])=[O:4])[CH:12]=2)=[CH:23][CH:22]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 20 °C
Procedure
Potassium hydroxide (1.105 g, 19.7 mmol) is added to a solution of [3-(4′-chloro-4-methyl-biphenyl-3-yl)-1,1-dimethylprop-2-ynyloxy]acetic acid methyl ester (6.7 g, 18.8 mmol) in dioxane (20 ml) and water (20 ml). After stirring for four hours at 20° C., the reaction mixture is extracted twice with dichloromethane. The aqueous layer is acidified at 0° C. to pH 2-3 using 1N aqueous hydrochloric acid and extracted twice with ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated in vacuo. The residue is stirred in hexane and filtered to afford [3-(4′-chloro-4-methylbiphenyl-3-yl)-1,1-dimethylprop-2-ynyloxy]acetic acid (4.50 g) as a white solid (m.p. 125° C.).
Workup
- extractionthe reaction mixture is extracted twice with dichloromethane
- customis acidified at 0° C. to pH 2-3
- extractionextracted twice with ethyl acetate
- dry with materialThe combined organic extracts are dried over anhydrous sodium sulfate
- filtrationfiltered
- customthe filtrate evaporated in vacuo
- stirringThe residue is stirred in hexane
- filtrationfiltered
Sources & evidence
- ORD record
- ord-fee932b76904471eb54a3fa3870d8f90
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680012B2
Reaction notes
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