Hydrochloric Acid → 3-((3-Methoxyphenyl)methyl)cyclohexanone

HRID 377309Notes

Reaction equation

HRID 377309 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][Mg]Cl.[C:12]1(=[O:18])[CH2:17][CH2:16][CH2:15][CH:14]=[CH:13]1.C[Si](Cl)(C)C.Cl>O1CCCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[CH2:6][CH:14]1[CH2:15][CH2:16][CH2:17][C:12](=[O:18])[CH2:13]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 135942-Cyclohexen-1-oneHCID 178490222HCID 178490222, compound

Product 1

HCID 193584913-((3-Methoxyphenyl)methyl)cyclohexanoneYield 49.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-methoxybenzylmagnesium chloride (19.8 mole) in tetrahydrofuran (20 ml) was added a mixture of 2-cyclohexen-1-one (1.9 g) and trimethylsilyl chloride (5.8 ml) in tetrahydrofuran (30 ml) at -78° C. under N2. The mixture was stirred for 1 hour at 0° C. The reaction mixture was poured into a mixture of ethyl acetate and 1N-hydrochloric acid and the organic layer was washed with saturated sodium bicarbonate aqueous solution and brine. The combined organic extracts were concentrated and the residue was purified by column chromatography on silica gel to give 3-(3-methoxybenzyl)cyclohexanone (2.12 g).

Workup

  1. washthe organic layer was washed with saturated sodium bicarbonate aqueous solution and brine
  2. concentrationThe combined organic extracts were concentrated
  3. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f7d8ff0ef89e4174b799a4d5af5f0e00
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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