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

HRID 70734

Reaction equation

HRID 70734 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. (tic 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-0429cb5177df4842bda314261e740f4f
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Linked notes

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