4,4-DIMETHYL-3,4-DIHYDRO-2H-NAPHTHALEN-1-ONE

Colourless Liquid

STR48 3, 4-Dihydro-4, 4-dimethyl-1(2H)-naphthalenone A solution of aluminum chloride (150 g) in 230 ml benzene was cooled in an ice bath and treated via a dropping funnel with a solution of the compound from Example 38 (40 g, 0.35 mole) in 70 ml benzene. After addition was completed, the reaction mixture was refluxed for 3 hours, then cooled and added slowly to conc. HCl in ice. The organic layer was separated, combined with an ether wash of the aqueous phase, and then washed successively with 1N HCl, water and saturated sodium bicarbonate. After drying the solvent was evaporated and the residue was distilled to give the title compound (50.5 g, 83%).4, 4-Dimethyl-1-tetralone (V) To a solution of anhydrous aluminum chloride (0.446 mmol, 59.36 g) in anhydrous benzene (94.0 mL) at 5 C. was added over a period of 45 minutes 5, 5-dimethyldihydrofuran-2-one (0.149 mole, 17.0 g). The reaction mixture was then slowly warmed to 90-100 C. After 3 hours, the mixture was quenched with ice water, 1N HCl and ethyl acetate at 0 C. The organic phase was then separated and concentrated in vacuo. The residue was chromatographed (eluted with 3% ethyl acetate in hexane) on silica gel to give 18.70 g (Y: 72%) of 4, 4-Dimethyl-1-tetralone (V) To a solution of anhydrous aluminum chloride (0.446 mmol, 59.36 g) in anhydrous benzene (94.0 mL) at 5 C. was added over a period of 45 minutes 5, 5-dimethyldihydrofuran-2-one (0.149 mole, 17.0 g). The reaction mixture was then slowly warmed to 90-100 C. After 3 hours, the mixture was quenched with ice water, 1N HCl and ethyl acetate at 0 C. The organic phase was then separated and concentrated in vacuo. The residue was chromatographed (eluted with 3% ethyl acetate in hexane) on silica gel to give 18.70 g (Y: 72%) of

Intermediate in the production of high affinity retinoic acid receptor (RAR) antagonists.

Molecular Weight:174.24
XLogP3:2.9
Hydrogen Bond Acceptor Count:1
Exact Mass:174.104465066
Monoisotopic Mass:174.104465066
Topological Polar Surface Area:17.1
Heavy Atom Count:13
Complexity:217
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes