Potassium Carbonate → 4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one

HRID 2089493Notes

Reaction equation

HRID 2089493 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]1[O:13]C(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.ClCCl.C(OCC)(=O)C>[OH:13][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10](=[O:12])[CH2:11][C:2]1([CH3:17])[CH3:1]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 59199404HCID 59199404, compound

Product 1

HCID 135275814-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of acetic acid 2,2-dimethyl-4-oxo-1,2,3,4-tetrahydro-naphthalen-1-yl ester (4.03 g, 16.7 mmol) in methanol (50 mL) and dichloromethane (10 mL) is added potassium carbonate (2.33 g, 16.66 mmol). The reaction is permitted to stir for 8 hours at which time it is diluted with ethyl acetate and the resulting solution is washed successively with water and brine. The aqueous phases are then back-extracted with dichloromethane and the organic phases are then combined, dried over magnesium sulfate, filtered, and concentrated to furnish 4-hydroxy-3,3-dimethyl-3,4-dihydro-2H-naphthalen-1-one; 1H NMR (400 MHz, CDCl3) δ ppm 1.04 (s, 3 H), 1.11 (s, 3 H), 2.07 (d, J=6.1 Hz, 1 H), 2.46 (d, J=16. 7 Hz, 1 H), 2.78 (d, J=16.7 Hz, 1 H), 4.64 (d, J=5.8 Hz, 1 H), 7.38-7.46 (m, 1 H), 7.59-7.63 (m, 2 H), 8.02 (d, J=7.8 Hz, 1 H).

Workup

  1. washthe resulting solution is washed successively with water and brine
  2. extractionThe aqueous phases are then back-extracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-612167ca1df44000810c6aec54cf1627
Source dataset
uspto-grants-2013_05
Patent number
US08436035B2

Reaction notes

Loading…