Reaction #1486

Reaction equation

methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate

methyl 5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate

Compound E2

methyl 5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate

sodiumhydroxide

HCl

→

title compound

5,5-Dimethyl-5,6dihydro-naphthalen-8(7H)-one

Solvents

ethanol

THF

Conditions

Workup

1. 1
   ExtractionThe mixture was extracted with ethyl acetate
2. 2
   Washthe combined organic layer was washed with water and brine
3. 3
   Dryingdried over MgSO4
4. 4
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure

Procedure

To a solution of methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate (Compound E2, 1.05 g, 4.5 mmol) in 10 mL of ethanol and THF (10 mL) was added sodiumhydroxide 9 mL (1M solution). The solution was stirred for 16 h and thereafter acidified with 10% HCl. The mixture was extracted with ethyl acetate, the combined organic layer was washed with water and brine, and dried over MgSO4. The solvent was distilled off under reduced pressure to afford the title compound as a white solid. 1H NMR (Acetone-D6): δ 1.44 (s, 6H), 2.07 (t, J=6.7 Hz, 2H), 2.73 (t, J=6.7 Hz, 2H), 7.70 (d, J=8.2 Hz, 1H), 8.19 (dd, J=1.9, 8.2 Hz, 1H), 8.57 (d, J=1.9 Hz, 1H).

Source