Hydrochloric Acid → Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[C:6]([F:12])[C:7]=1[O:8]COC.Cl.O>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH:5]=[C:6]([F:12])[C:7]=1[OH:8]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a solution of ethyl 3,5-difluoro-4-(methoxymethoxy)benzenepropanoate (2.3 g, 8.4 mmol) in ethanol (12 mL) was added hydrochloric acid (0.5 mL), and the mixture was stirred at 50° C. for 1 hour. After the reaction solution was returned to room temperature, water was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water, and then concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=9:1 to 1:1) to give the title compound (1.7 g, yield 88%).
Workup
- customwas returned to room temperature
- extractionthe reaction mixture was extracted with ethyl acetate
- washThe extract was washed with water
- concentrationconcentrated under reduced pressure
- customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=9:1 to 1:1)
Sources & evidence
- ORD record
- ord-643d5899cea94a40bfff40e02dd6a11f
- Source dataset
- uspto-grants-2011_08
- Patent number
- US08008525B2
Reaction notes
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