Carbon Dioxide → 6-Methoxy-2-Naphthoic Acid
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([O:12][CH3:13])[CH:6]=[CH:5]2.C([Li])(C)(C)C.[C:19](=[O:21])=[O:20]>C1COCC1>[CH3:13][O:12][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[CH:3]=[C:2]([C:19]([OH:21])=[O:20])[CH:11]=[CH:10]2Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
A solution of 8.00 g (33.8 mmol, Aldrich) of 6-bromo-2-methoxynaphthalene in 75 ml of dry THF was cooled to -78° C. and 36 ml (1.8M in pentane, 65 mmol, Aldrich) of t-butyllithium was added over 30 minutes. The reaction mixture was stirred for 30 minutes at -78° C. then warmed to -20° C. for 30 minutes. The mixture was recooled to -78° C. and 8.00 g (180 mmol) of crushed dry ice was added to the slurry, and then this was allowed to warm to room temperature over 2 hours. The mixture was concentrated in vacuo, 100 ml of 1N HCl was added to the residue and this was extracted with 100 ml of hot EtOAc. The organic layer was washed with water, dried (MgSO4) and concentrated in vacuo to give a solid. Purification via recrystallization (EtOAc/petroleum ether) afforded 5.80 g (85%) of the title compound as small white needles: m.p. 198°-200° C.
Workup
- temperaturethen warmed to -20° C. for 30 minutes
- customwas recooled to -78° C.
- temperatureto warm to room temperature over 2 hours
- concentrationThe mixture was concentrated in vacuo, 100 ml of 1N HCl
- additionwas added to the residue
- extractionthis was extracted with 100 ml of hot EtOAc
- washThe organic layer was washed with water
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- customto give a solid
- customPurification
- customvia recrystallization (EtOAc/petroleum ether)
Sources & evidence
- ORD record
- ord-77701bf78bb6402ca5cd89fd32a5e9e8
- Source dataset
- uspto-grants-1990_03
- Patent number
- US04910208
Reaction notes
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