Sodium Hydroxide → 3-[4-(2-Fluorophenyl)benzoyl]propanoic acid
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:21])[CH2:15][CH2:16][C:17]([O:19]C)=[O:18])=[CH:10][CH:9]=1.[OH-].[Na+]>O1CCCC1.CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:21])[CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[CH:10][CH:9]=1Participants
Procedure
To a stirred solution of 4-(2′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester (7.17 g, 0.0250 mol) in tetrahydrofuran (60 mL) at room temperature was added a solution of sodium hydroxide (1.04 g, 0.026 mol) in methanol (60 mL), and the mixture was stirred for 23 hours. To the reaction was added 1.0 M aqueous sodium hydroxide (10 mL), and the mixture was stirred for an additional 24 hours. The mixture was rotary evaporated, and the residue was partitioned between water and chloroform. The aqueous layer was washed with chloroform (3×) and acidified with concentrated hydrochloric acid to pH=3. The resulting solids were filtered, washed with dilute aqueous hydrochloric acid (pH=3), and dried under house vacuum (air bleed) to give 6.51 g of 4-(2′-fluoro-biphenyl-4-yl)-4-oxo-butyric acid as a pale yellow solid; mp 148-153° C.
Workup
- stirringthe mixture was stirred for an additional 24 hours
- customthe residue was partitioned between water and chloroform
- washThe aqueous layer was washed with chloroform (3×)
- filtrationThe resulting solids were filtered
- washwashed with dilute aqueous hydrochloric acid (pH=3)
- customdried under house vacuum (air bleed)
Sources & evidence
- ORD record
- ord-a6d54717dcdc44de88a92d9065fc80b0
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06239288B1
Reaction notes
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