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

HRID 2415603Notes

Reaction equation

HRID 2415603 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 died 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. customRemoval of the solvents under pressure

Sources & evidence

ORD record
ord-04836b26a82941a589c8f6fc5636e3de
Source dataset
uspto-grants-2004_11
Patent number
US06818775B2

Reaction notes

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