Hydrochloric Acid → 2-Fluoro-5-hydroxy-4-methylphenol
Reaction equation
C(=O)([O-])[O-].[K+].[K+].C(=O)(OC)[O:8][C:9]1[CH:14]=[C:13]([OH:15])[C:12]([F:16])=[CH:11][C:10]=1[CH3:17].Cl>CO>[F:16][C:12]1[CH:11]=[C:10]([CH3:17])[C:9]([OH:8])=[CH:14][C:13]=1[OH:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Potassium carbonate (870 mg, 6.3 mmol) was added to a solution of (4-fluoro-5-hydroxy-2-methylphenyl) methyl carbonate (1.2 g, 6 mmol) in methanol (20 ml) and the mixture was heated at 50° C. for 1 hour. The mixture was allowed to cool, adjusted to pH3 with hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with brine, dried (MgSO4) and the volatiles removed by evaporation. The residue was purified by column chromatography eluting with petroleum ether/ethyl acetate (7/3) to give 2-fluoro-5-hydroxy-4-methylphenol (603 mg, 70%) as a yellow solid.
Workup
- temperatureto cool
- extractionextracted with ethyl acetate
- washThe combined extracts were washed with brine
- dry with materialdried (MgSO4)
- customthe volatiles removed by evaporation
- customThe residue was purified by column chromatography
- washeluting with petroleum ether/ethyl acetate (7/3)
Sources & evidence
- ORD record
- ord-35827393192649578d29c5c3ec8ece2a
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809097B1
Reaction notes
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