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

HRID 963897Notes

Reaction equation

HRID 963897 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.C1COCC1>[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

6

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 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

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 THF (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-11e561b6568141ff915f4f2d79a2666e
Source dataset
uspto-grants-1998_06
Patent number
US05763635

Reaction notes

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