Water → 1-Cyclohexyl-2-phenylethanone

HRID 969942Notes

Reaction equation

HRID 969942 reaction equation
CN(OC)[C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[CH2:13]([Mg]Cl)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(OCC)C.O>O1CCCC1>[CH2:13]([C:3]([CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 11769007N-methoxy-N-methylcyclohexanecarboxamideHCID 178418336HCID 178418336, compound

Product 1

HCID 27946121-Cyclohexyl-2-phenylethanoneYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of N-methyl-N-methoxy cyclohexanecarboxamide (7.42 mmol) in 30 mL of tetrahydrofuran at 0° C. under nitrogen was added a solution of benzyl magnesium chloride (2.0 M in tetrahydrofuran, 4.5 mL, 9.0 mmol). The mixture was stirred at 0° C. for 30 minutes and at room temperature for 1 hour. Diethyl ether (50 mL) and water (20 mL) were added. The organic layer was separated, dried, filtered, and concentrated. Purification of the residue by flash chromatography using hexanes and ethyl acetate gave cyclohexyl benzyl ketone (1.05 g) in 70% yield as oil.

Workup

  1. customThe organic layer was separated
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-d8a7af15bcb047d88b8e7e33b453f487
Source dataset
uspto-grants-2007_12
Patent number
US07309702B2

Reaction notes

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