Ethyl Acetate → 6-methoxy-4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 2089497Notes

Reaction equation

HRID 2089497 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:19])[CH2:8][C:9]([CH3:18])([CH3:17])[CH:10]2[O:13]C(=O)C)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].C(OCC)(=O)C>ClCCl.CO>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:19])[CH2:8][C:9]([CH3:17])([CH3:18])[CH:10]2[OH:13]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 59199424Acetic acid 7-methoxy-2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl ester

Product 1

HCID 675467026-methoxy-4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of acetic acid 7-methoxy-2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl ester (0.94 g, 3.44 mmol) in dichloromethane (2 mL) and methanol (10 mL) is added K2CO3 (0.48 g, 3.44 mmol) and the mixture is vigorously stirred for 8 hours. Ethyl acetate is added and the mixture is washed twice with water and brine. The aqueous phases are back-extracted once with dichloromethane and the combined organic phase is dried over magnesium sulfate, filtered, and concentrated to afford 6-methoxy-4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one, which is used in the next step without further purification.

Workup

  1. washthe mixture is washed twice with water and brine
  2. extractionThe aqueous phases are back-extracted once with dichloromethane
  3. dry with materialthe combined organic phase is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a39039265878438db458e0ea3a4ebd12
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

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