Water → 6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](Cl)=[O:10])=[CH:4][CH:3]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:16]=[CH2:17].O>ClCCl>[F:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[CH2:8][C:9](=[O:10])[CH2:17][CH2:16]2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
p-Fluorophenylacetyl chloride (17.25 g) in dichloromethane (100 ml) was added dropwise to aluminium chloride (26.7 g) suspended in dichloromethane (400 ml) maintained at -10° C. by cooling in a solid carbon dioxide/acetone bath. Ethylene gas was then passed through the mixture for 15 minutes while maintaining the temperature at -10° C. The mixture was then allowed to warm to room temperature and stirred for 3 hours. The mixture was then cooled to 5°-10° C. and ice and water (160 ml) added cautiously with stirring over a period of 45 minutes. The dichloromethane was then separated and washed successively with dilute hydrochloric acid, (150 ml×2), sodium bicarbonate solution (150 ml×2) and brine. The dichloromethane was then dried and evaporated. The residue was distilled to give 6-fluoro-2-tetralone (12.81 g) with a boiling range of 68°-76° C./0.05 Torr. The distillatte crystallised on standing.
Workup
- temperatureby cooling in a solid carbon dioxide/acetone bath
- temperaturewhile maintaining the temperature at -10° C
- temperatureto warm to room temperature
- temperatureThe mixture was then cooled to 5°-10° C.
- stirringwith stirring over a period of 45 minutes
- customThe dichloromethane was then separated
- washwashed successively with dilute hydrochloric acid, (150 ml×2), sodium bicarbonate solution (150 ml×2) and brine
- dry with materialThe dichloromethane was then dried
- customevaporated
- distillationThe residue was distilled
Sources & evidence
- ORD record
- ord-8e6ca45ee8d64057883dda5c1863d336
- Source dataset
- uspto-grants-1984_02
- Patent number
- US04431834
Reaction notes
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