4-Carboxaldehydebenzocyclobutene
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4-Carboxaldehydebenzocyclobutene
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CAS No:
112892-88-3
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Formula:
C9H6O
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Chemical Name:
4-Carboxaldehydebenzocyclobutene
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Synonyms:
4-carboxaldehydebenzocyclobutene;Bicyclo[4.2.0]octa-1,3,5-triene-3-carbaldehyde;4-CHOBCB4-Carboxaldehydebenzocyclobutene;Bicyclo[4.2.0]octa-1,3,5-triene-3-carboxaldehyde
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CAS No:
4-Carboxaldehydebenzocyclobutene Use and Manufacturing
3-Carboxaldehydebicyclo[4, 2, 0]octa- 1 , 3;5-triene or A- Carboxaldehydebenzocyclobutene, Q6. To a 500-mL flask was added '50 mL dry of THF, Mg turnings (2.88 g, 120 mmol), and 1, 2-dibromoethane (4 drops). The reaction mixture was then heated under reflux for 15 min, 4-Bromobenzocyclobutene, 5, 1 1 (20.0 g, 109 mmol) in 25 mL THF was added via a dropping funnel to form the Grignard reagent. After addition and rinsing the dropping funnel with 25 mL of dry THF, the reaction mixture was heated for an additional 45 min under reflux to give a green brown solution. The reaction mixture was then cooled to 0 Under a nitrogen atmosphere, bromide 3 (3.0 g, 16.3 mmol) and 50 ml of anhydrous tetrahydrofuran were charged in a 50 ml recovery flask. After cooling to -78°C under a nitrogen gas flow, 11.3 ml (18.0 mmol) of an n-butyl lithium hexane solution (1.59 M) was added dropwise, followed by stirring at the same temperature for 30 minutes. Then, 2.40 g of anhydrous dimethylformamide was added dropwise in the recovery flask, followed by stirring at the same temperature for 30 minutes, heating to room temperature and further stirring for 1 hour. The reaction liquid was poured into 100 ml of water and the oil phase was extracted twice with 50 ml of ethyl acetate, and then the oil phase was dried over anhydrous magnesium sulfate. After isolating the magnesium compound by filtration, the oil phase was concentrated under reduced pressure using an evaporator and the obtained residue was purified by silica gel chromatography (Wakosil C-300, eluent: hexane/ethyl acetate = 3 : 1 (volume ratio)) to obtain 1.54 g (yield: 71.1percent) of aldehyde 4 as the objective product.
Computed Properties
Molecular Weight:132.16
XLogP3:0.9
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:132.057514874
Monoisotopic Mass:132.057514874
Topological Polar Surface Area:17.1
Heavy Atom Count:10
Complexity:142
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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4-Carboxaldehydebenzocyclobutene
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