Fluorobenzene → 2-(4-Fluorobenzoyl)-naphthalene-3-carboxylic acid
Reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]2[C:11]([O:13][C:14](=[O:15])[C:2]=12)=[O:12].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[Cl-].[Al+3].[Cl-].[Cl-]>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:11]([C:3]2[C:2]([C:14]([OH:13])=[O:15])=[CH:1][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=2)=[O:12])=[CH:19][CH:18]=1Participants
Procedure
45.0 g (227 mmol) of 2,3-naphthalenedicarboxylic acid anhydride are suspended in 200 ml (2.1 moles) of fluorobenzene. 75.5 g (565 mmol) of powdered aluminium chloride are added in the course of 5 minutes, with vigorous stirring (exothermic reaction up to about 32° C.). The dark red suspension is refluxed and stirred for 6 hours. The solution is then allowed to cool to room temperature and is poured onto about 500 g of ice, and is stirred to bring the hydrolysis to completion. Excess fluorobenzene is evaporated off and the resulting product is suspended in water. The suspension is filtered, the filtrate is rinsed with water and the product is dried. 76 g of crude 2-(4-fluorobenzoyl)-naphthalene-3-carboxylic acid are obtained. The crude product is stirred with 2 liters of 10% sodium carbonate solution, the resulting solution is acidified with hydrochloric acid and the white precipitate is filtered off and dried. 54.2 g (81% of theory) of 2-(4-fluorobenzoyl)-naphthalene-3-carboxylic acid are obtained.
Workup
- custom(exothermic reaction up to about 32° C.)
- temperatureThe dark red suspension is refluxed
- stirringstirred for 6 hours
- stirringis stirred
- customthe hydrolysis to completion
- customExcess fluorobenzene is evaporated off
- filtrationThe suspension is filtered
- washthe filtrate is rinsed with water
- customthe product is dried
Sources & evidence
- ORD record
- ord-0ff564ee45564632a2bab757242902bb
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04601853
Reaction notes
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