Reaktion #1493

Reaktionsgleichung

methyl 5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylate

Compound E18

methyl 5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylate

NaOH

→

title compound

5,5-Dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylic acid

Lösungsmittel

EtOH

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas quenched by the addition of 10% aqueous HCl
2. 2
   ExtraktionThe mixture was extracted with EtOAc
3. 3
   Waschenthe combined organic layers washed with H2O and saturated aqueous NaCl
4. 4
   Trocknenbefore being dried over Na2SO4
5. 5
   SonstigeRemoval of the solvents under pressure

Vorschrift

To a solution of methyl 5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylate (Compound E18, 300.0 mg, 0.926 mmol) in 4.0 mL of EtOH and 2.0 mL THF was added NaOH (200.0 mg, 5.00 mmol; 5.0 mL of a 1N aqueous solution). After stirring overnight at room temperature the reaction was quenched by the addition of 10% aqueous HCl. The mixture was extracted with EtOAc and the combined organic layers washed with H2O and saturated aqueous NaCl before being dried over Na2SO4. Removal of the solvents under pressure afforded the title compound as a yellow solid.

Quelle