Hydrochloric Acid → HCID 12039786, compound

HRID 1108760Notes

Reaction equation

HRID 1108760 reaction equation
[Mg].Br[C:3]1[CH:4]=[C:5]([O:9][CH3:10])[CH:6]=[CH:7][CH:8]=1.II.[C:13]1(=[O:19])[CH2:18][CH2:17][CH2:16][CH:15]=[CH:14]1.Cl>O1CCCC1.[Cu]Br>[CH3:10][O:9][C:5]1[CH:4]=[C:3]([CH:15]2[CH2:16][CH2:17][CH2:18][C:13](=[O:19])[CH2:14]2)[CH:8]=[CH:7][CH:6]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 135942-Cyclohexen-1-oneHCID 169713-BromoanisoleHCID 5462224Magnesium

Product 1

HCID 12039786HCID 12039786, compoundYield 47.6%

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Grignard reagent was prepared from magnesium (2.8 g) and 3-bromoanisole (22.0 g) in tetrahydrofuran (50 ml) in the presence of iodine, and a catalytic amount of copper (I) bromide (CuBr, 0.83 g) was added thereto. A tetrahydrofuran (10 ml) solution containing 2-cyclohexen-1-one (9.6 g) was also added dropwise while stirring on ice. After stirring at room temperature for 3 hours, hydrochloric acid was added, and extraction was performed with ethyl acetate. After drying with anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to produce a light yellow oily substance which was then separated and purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1) to give 9.7 g of 3-(3-methoxyphenyl)cyclohexanone (47.6% yield).

Workup

  1. additionwas also added dropwise
  2. stirringAfter stirring at room temperature for 3 hours
  3. extractionextraction
  4. dry with materialAfter drying with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto produce a light yellow oily substance which
  7. customwas then separated
  8. custompurified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-9fcaa48c63bd47528ac6770364730b85
Source dataset
uspto-grants-2000_05
Patent number
US06069176

Reaction notes

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