Hydrochloric Acid → 3-(3-Fluoro-4-hydroxyphenyl)propionic acid
Reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[O:9]C>N1C=CC=CC=1>[F:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH:6]=[CH:7][C:8]=1[OH:9]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 190 °C
Procedure
A pyridine/hydrochloric acid complex prepared by mixing pyridine and concentrated hydrochloric acid (30 ml each) and then heating the mixture at 190° C. for 1 hour was added with Intermediate 19 (2.40 g) and stirred at 190° C. for 1.5 hours. The reaction mixture was poured into ice cooled 1 N hydrochloric acid (100 ml) and extracted with ethyl acetate (200 ml). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain the title compound (Intermediate 20, 1.98 g).
Workup
- customA pyridine/hydrochloric acid complex prepared
- additionThe reaction mixture was poured into ice
- extractionextracted with ethyl acetate (200 ml)
- washThe organic layer was washed with saturated brine
- customdried
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-9eee419c62cd4a1a9d4b42ab4984bcdf
- Source dataset
- uspto-grants-2005_03
- Patent number
- US06867320B2
Reaction notes
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