Reaction #1493

Reaction equation

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

Solvents

EtOH

THF

Conditions

Workup

1. 1
   Otherwas quenched by the addition of 10% aqueous HCl
2. 2
   ExtractionThe mixture was extracted with EtOAc
3. 3
   Washthe combined organic layers washed with H2O and saturated aqueous NaCl
4. 4
   Dryingbefore being dried over Na2SO4
5. 5
   OtherRemoval of the solvents under pressure

Procedure

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.

Source