Acetone → 6-Fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid methyl ester
Reaction equation
C(=O)([O-])[O-].[K+].[K+].O.CC(C)=O.[CH3:12][O:13][C:14]([C:16]1[C:25]([CH3:26])=[C:24]([O:27]C(=O)C)[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([F:31])[CH:22]=2)[CH:17]=1)=[O:15]>CO>[CH3:12][O:13][C:14]([C:16]1[C:25]([CH3:26])=[C:24]([OH:27])[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([F:31])[CH:22]=2)[CH:17]=1)=[O:15]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A heterogeneous mixture of potassium carbonate (46 g, 0.33 mol), water (260 mL), and acetone (260 mL) was added in three portions to a 0° C. solution of 4-acetoxy-6-fluoro-3-methyl-naphthalene-2-carboxylic acid methyl ester (18.4 g, 0.066 mol) in methanol (1 L). The resulting mixture was stirred at 0° C. for 15 minutes, then warmed to room temperature and stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo. The remaining oily suspension was diluted with ethyl acetate and washed with 1 N aqueous HCl. The organic phase was dried (MgSO4), filtered, and concentrated to yield 9.64 g (62%) of 6-fluoro-4-hydroxy-3-methyl-naphthalene-2-carboxylic acid methyl ester as a yellowish tan solid. HRMS (ES−) cald. for C13H11FO3 [(M−H)−] 233.0619, obsd. 233.0619.
Workup
- temperaturewarmed to room temperature
- stirringstirred at room temperature for 1 hour
- concentrationThe reaction mixture was concentrated in vacuo
- additionThe remaining oily suspension was diluted with ethyl acetate
- washwashed with 1 N aqueous HCl
- dry with materialThe organic phase was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-5c58ed271f5c4bb2a05712e986da6f52
- Source dataset
- uspto-grants-2012_02
- Patent number
- US08124629B2
Reaction notes
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