Sodium Hydroxide → 2-Chloro-5-fluoro-4-methylbenzoic acid
Reaction equation
C[O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([F:10])[C:7]([CH3:11])=[CH:6][C:5]=1[Cl:12].[OH-].[Na+]>CO>[Cl:12][C:5]1[CH:6]=[C:7]([CH3:11])[C:8]([F:10])=[CH:9][C:4]=1[C:3]([OH:13])=[O:2]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A solution of 2-chloro-5-fluoro-4-methyl-benzoic acid methyl ester (Preparation 1a, 57.77 g) in methanol (400 mL) was treated with sodium hydroxide 2 M solution (285 mL) under nitrogen. The resulting mixture was stirred at 25° C. for 1 h. The reaction mixture was extracted with diethyl ether (discarded) and the aqueous layer diluted with 2 M hydrochloric acid (250 mL). The reaction mixture was extracted with ethyl acetate (500 mL). The combined organics were dried (MgSO4), filtered and evaporated to afford the subtitle compound (51.6 g).
Workup
- extractionThe reaction mixture was extracted with diethyl ether (discarded)
- additionthe aqueous layer diluted with 2 M hydrochloric acid (250 mL)
- extractionThe reaction mixture was extracted with ethyl acetate (500 mL)
- dry with materialThe combined organics were dried (MgSO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-0350091822ef459fa255ed6c24ee4d47
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969350B2
Reaction notes
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