Methyl iodide → 1-(4-Bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl) ethanone

HRID 2180592Notes

Reaction equation

HRID 2180592 reaction equation
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:14](=[O:16])[CH3:15])[C:3]=1[OH:17].[C:18](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O.O>[Br:1][C:2]1[C:11]2[C:10]([CH3:12])([CH3:13])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:14](=[O:16])[CH3:15])[C:3]=1[O:17][CH3:18]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 224908841-(4-Bromo-3-hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone

Product 1

HCID 224910531-(4-Bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl) ethanone

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 1-(4-bromo-3-hydroxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanone (Compound A-91, 11.8 g, 39.7 mmol), potassium carbonate (14.4 g, 119.1 mmol) in acetone (350 mL) was added methyl iodide (19.8 mL, 317.6 mmol). After heating to reflux for 16 h, the mixture was cooled to room temperature, diluted with water and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo to give the title compound as a yellow oil. The material was used in the next step without further purification.

Workup

  1. temperatureAfter heating
  2. temperatureto reflux for 16 h
  3. extractionextracted with diethyl ether
  4. washThe combined ethereal layers were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f741ea382cf947f3b25a9aeb7ec0ae8a
Source dataset
uspto-grants-2005_05
Patent number
US06887896B1

Reaction notes

Loading…