Hydrochloric Acid → HCID 54471994, compound
Reaction equation
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:4][C:3]=1[C:18]1[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=1)[CH:21]=[CH:22][C:23]([OH:25])=[O:24].C1COCC1.C([Li])CCC.Cl>O.CCCCCC>[CH2:13]([O:12][C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:2]=[C:3]([C:18]2[CH:19]=[C:20]([CH:26]=[CH:27][CH:28]=2)[CH:21]=[CH:22][C:23]([OH:25])=[O:24])[CH:4]=1)[CH2:14][CH2:15][CH2:16][CH3:17]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
3-(1-Bromo-4-pentyloxynaphthalene-2-yl)cinnamic acid (100 mg, 0.275 mmol) and THF (2 ml) were mixed in a reaction vessel replaced with argon, and this solution was cooled to -78° C. A hexane solution (1.6M, 0.38 ml) of n-butyllithium (0.6 mmol) was added, and the mixture was stirred for 1 hour. Water (1 ml) and conc. hydrochloric acid were added to make this solution acidic (pH=1), and the aqueous layer was extracted 4 times with ethyl acetate (5 ml). The organic layers were combined, washed 3 times with saturated brine (5 ml), and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by column chromatography (hexane/ethyl acetate=2/1) to give 3-(4-pentyloxynaphthalene-2-yl)cinnamic acid (46.2 mg, 59%) as colorless crystals.
Workup
- extractionthe aqueous layer was extracted 4 times with ethyl acetate (5 ml)
- washwashed 3 times with saturated brine (5 ml)
- dry with materialdried over anhydrous magnesium sulfate
- filtrationThe drying agent was filtered off
- concentrationthe filtrate was concentrated under reduced pressure
- customThe obtained residue was purified by column chromatography (hexane/ethyl acetate=2/1)
Sources & evidence
- ORD record
- ord-059b97a2a2fb4f8dae1116bf35de8298
- Source dataset
- uspto-grants-2000_01
- Patent number
- US06017919
Reaction notes
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