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

HRID 1397

Reaction equation

HRID 1397 reaction equation
[CH3:1][C:2]1([CH3:23])[CH2:11][CH:10]=[C:9]([S:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]2[CH:7]=[C:6]([C:19]([O:21]C)=[O:20])[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+]>CCO.C1COCC1>[CH3:1][C:2]1([CH3:23])[CH2:11][CH:10]=[C:9]([S:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]2[CH:7]=[C:6]([C:19]([OH:21])=[O:20])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22571588Methyl 5,5-dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylate2×

Product 1

HCID 225715435,5-Dimethyl-5,6-dihydro-8-(phenylthio)-naphthalene-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

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.

Workup

  1. customwas quenched by the addition of 10% aqueous HCl
  2. extractionThe mixture was extracted with EtOAc
  3. washthe combined organic layers washed with H2O and saturated aqueous NaCl
  4. dry with materialbefore being dried over Na2SO4
  5. customRemoval of the solvents under pressure

Sources & evidence

ORD record
ord-e3e7b7ca98e641d6a2d408b95787c8d2
Source dataset
uspto-grants-1998_03
Patent number
US05723666

Linked notes

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