Carbon Dioxide → 1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde

Participants

Role	Name	HCID	Charge
Reactant	Carbon Dioxide	HCID 280	—
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Pentane	HCID 8003	—
Reactant	6-Bromo-1,1-dimethyl-4-p-tolyl-1,2-dihydronaphthalene	HCID 10687622	—
Reactant	HCID 178418306	HCID 178418306	—
Solvent	Tetrahydrofuran	HCID 8028	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	1-(Tol-4-yl)3,4-dihydro-4,4-dimethyl-7-naphthaldehyde	HCID 86588677	—

Reaction Steps

To a cold (-78° C.), stirred solution of 1-(tol-4-yl)3,4-dihydro-4,4-dimethyl-7-bromo-naphthalene (Compound B 1 g, 3.2 mmol), in THF (17 mL) was added t-BuLi in pentane (1.7M solution, 3 mL, 5.1 mmol). After 10 minutes dry dimethylformamide (DMF) (600 mg, 8 mmol) was added and the dry-ice cooling was replaced with ice-water bath. The mixture was gradually warmed to ambient temperature and diluted with ethylacetate (150 mL), washed with water (15 mL). The organic layer was dried with MgSO4 and solvent was removed under reduced pressure. The crude material was purified by silicagel chromatography to afford the title compound as a white solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05728846
Source dataset	uspto-grants-1998_03
ORD ID	ord-bf0cea00f0c14b87bedbeafd627d9061
Source note	uspto-grants-1998_03