Methyl iodide → 1-Methoxy-4-(1-phenyl-cyclohexyl)-benzene

HRID 1170549

Reaction equation

HRID 1170549 reaction equation
[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:22]I>CN(C=O)C>[CH3:22][O:19][C:16]1[CH:15]=[CH:14][C:13]([C:7]2([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15384544-(1-Phenylcyclohexyl)phenol

Product 1

HCID 116805591-Methoxy-4-(1-phenyl-cyclohexyl)-benzene

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(1-phenylcyclohexyl)phenol (20 mg, 0.08 mmol) was dissolved in DMF (2 mL). A suspension of NaH in oil (60%, 5 mg, 0.125 mmol) was added. After stirring for 5 minutes methyl iodide (0.05 mL; 0.8 mmol) was added. The reaction mixture was stirred for 2 h. (tlc indicated full conversion of the starting material) then quenched with water (10 mL). Dichloromethane (10 mL) was added. The mixture was shaken and the organic phase separated off, dried (Na2SO4) and concentrated to syrup. The title product was afforded after work-up by flash-chromatography (eluent dichloromethane). Yield: 20 mg, quantitatively. LC-MS purity (UV/MS): 100/-, Rt 6.48 min. 1H NMR data were in accordance with the data written above.

Workup

  1. additionwas added
  2. additionwas added
  3. customthen quenched with water (10 mL)
  4. additionDichloromethane (10 mL) was added
  5. stirringThe mixture was shaken
  6. customthe organic phase separated off
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to syrup

Sources & evidence

ORD record
ord-47afb7bca2d1494e8e29f205685d8142
Source dataset
uspto-grants-2010_11
Patent number
US07825265B2

Linked notes

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