Tetralin → 5,6,7,8-tetrahydronaphthalene-2-carbaldehyde
Reaction equation
[CH2:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[CH3:11][O:12]C(Cl)Cl>[Ti](Cl)(Cl)(Cl)Cl>[CH:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[CH2:1][CH2:2][CH2:3][CH2:4]2)=[O:12]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound 12 was prepared by an alternate procedure as follows: Tetralin was formylated with dichloromethyl methyl ether and titanium tetrachloride catalyst to give 6-formyltetralin. Reaction of the aldehyde with malonic acid in the presence of an amine catalyst gave the substituted acrylic acid. Catalytic hydrogenation of the double bond gave the corresponding substituted propionic acid, 3-(6-tetralyl)propionic acid. Conversion of the acid to the acid chloride with phosphorus pentachloride followed by cyclization with aluminum chloride gave the desired 2,3,5,6,7,8-hexahydro-1H-benz[f]inden-1-one.
Sources & evidence
- ORD record
- ord-afc99b7e923a4e0ea8e74e257462e877
- Source dataset
- uspto-grants-1982_09
- Patent number
- US04351893
Reaction notes
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