4-Methoxybenzoic Acid → HCID 59389240, compound
Reaction equation
C([Li])(CC)C.[C:6]([OH:16])(=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.CN(CCN(C)C)C.[F:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][CH:36]=1)[C:29](OCC)=[O:30]>>[F:25][C:26]1[CH:27]=[C:28]([CH:34]=[CH:35][CH:36]=1)[C:29]([C:8]1[CH:9]=[C:10]([O:13][CH3:14])[CH:11]=[CH:12][C:7]=1[C:6]([OH:16])=[O:15])=[O:30]Participants
Procedure
s-Butyllithium (52 mL, 1.4 M in pentane, 72 mmol) was added at −78° C. over 90 min. to a solution of p-anisic acid (5 g, 33 mmol) and TMEDA (11 ml, 72 mmol) in THE (80 mL). After stirring for 15 min., ethyl 3-fluorobenzoate (5 mL, 40 mmol) was added in one portion. The reaction mixture was stirred for 15 min. then it was quenched with water (20 mL). The reaction mixture was then warmed to room temperature and poured into water (1.5 L) 1N NaOH (30 ml) was added and the reaction mixture was then extracted with EtOAc. The extracts were discarded. The aqueous phase was then acidified with conc. HCl to pH 1 and extracted with EtOAc. Drying (Na2SO4) and concentration gave a residue which was recrystallized from hexanes/EtOAc to give the title compound 59 as a white solid.
Workup
- stirringThe reaction mixture was stirred for 15 min.
- customit was quenched with water (20 mL)
- additionpoured into water (1.5 L) 1N NaOH (30 ml)
- additionwas added
- extractionthe reaction mixture was then extracted with EtOAc
- extractionextracted with EtOAc
- customDrying
- concentration(Na2SO4) and concentration
- customgave a residue which
- customwas recrystallized from hexanes/EtOAc
Sources & evidence
- ORD record
- ord-270b1181fb274d70893dab2b9f68404b
- Source dataset
- uspto-grants-2010_07
- Patent number
- US07763614B2
Reaction notes
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