Reaktion #411428

Reaktionsgleichung

ethyl 5′,6′-dihydro-5′,5′-dimethyl-8′-(4-methylphenyl)-2,2′-binaphthalene

Compound 64

Ethyl 5′,6′-dihydro-5′,5′-dimethyl-8′-(4-methylphenyl)-[2,2′-binaphthalene]-6-carboxylate

NaOH

HCl

→

pure material

5′,6′-Dihydro-5′,5′-dimethyl-8′-(4-methylphenyl)-[2,2′-binaphthalene]-6-carboxylic Acid

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe product was extracted into ethyl acetate
2. 2
   Waschenwashed with water, brine
3. 3
   Trocknendried (MgSO4)
4. 4
   Filtrationfiltered
5. 5
   Sonstigethe solvent removed in-vacuo
6. 6
   SonstigeThe residue was recrystalized from THF/ethyl acetate at 0° C.

Vorschrift

A solution of ethyl 5′,6′-dihydro-5′,5′-dimethyl-8′-(4-methylphenyl)-2,2′-binaphthalene]-6-carboxylate (Compound 64) 0.19 g, 0.43 mmol), EtOH (8 ml) and 1N aqueous NaOH (2 ml) was heated to 60° C. for 3 hours. The solution was cooled to 0° C. and acidified with 1N aqueous HCl. The product was extracted into ethyl acetate, and the organic layers combined, washed with water, brine, dried (MgSO4), filtered and the solvent removed in-vacuo. The residue was recrystalized from THF/ethyl acetate at 0° C. to give 35 mg of pure material. The mother liquor was concentrated under reduced pressure and the residue purified by silica gel chromatography (100% ethyl acetate) to give an additional 125 mg of the title compound (overall yield=160 mg, 90%) as a colorless solid. 1H NMR (DMSO-d6) δ 8.57 (s, 1H), 8.11 (d, 1H, J=8.7 Hz), 7.96-7.82 (overlapping d's, 3H),7.65 (d, 2H, J=7.6 Hz), 7.50 (d, 1H, J=7.9 Hz), 7.28 (s, 1H), 7.26 (d, 2H, J=8.3 Hz), 7.21 (d, 2H, J=8.3 Hz), 6.01 (t, 1H, J=4.5 Hz), 3.34 (br s, 1H), 2.31 (s, 3H), 2.31 (d, 2H, J=4.5 Hz), 1.31 (s, 6H).

Quelle