Hydrochloric Acid → 5,5-Dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

HRID 1268476Notes

Reaction equation

HRID 1268476 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9](=[O:12])[C:8]2[CH:7]=[C:6]([C:13]([O:15]C)=[O:14])[CH:5]=[CH:4][C:3]1=2.[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9](=[O:12])[C:8]2[CH:7]=[C:6]([C:13]([OH:15])=[O:14])[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10681077Methyl 5,5-dimethyl-5,6 dihydro-naphthalen-8(7h)-one-2-carboxylate2×

Product 1

HCID 154628445,5-Dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of methyl-5,5-dimethyl-5,6-dihydro-naphthalen-8(7H)-one-2-carboxylate (Compound E2, 1.05 g, 4.5 mmol) in 10 mL of ethanol and TBF (10 mL) was added sodiumhydroxide 9 mL (1M solution). The solution was stirred for 16 h and thereafter acidified with 10% HCl. The mixture was extracted with ethyl acetate, the combined organic layer was washed with water and brine, and dried over MgSO4. The solvent was distilled off under reduced pressure to afford the title compound as a white solid.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washthe combined organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-809bf1a24fa34b6890cd30c948c0dbf6
Source dataset
uspto-grants-2003_04
Patent number
US06555690B2

Reaction notes

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