Methyl iodide → HCID 178444452, compound

HRID 2226075Notes

Reaction equation

HRID 2226075 reaction equation
[CH2:1]([C@H:6]1[CH2:11][CH2:10][C@H:9]([CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)[CH2:8][CH2:7]1)[CH2:2][CH2:3][CH2:4][CH3:5].CI.[C:25](=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[CH3:25][O:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][CH2:14][CH2:13][CH2:12][C@H:9]2[CH2:8][CH2:7][C@H:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])[CH2:11][CH2:10]2)=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6569Methyl Ethyl KetoneHCID 11430Potassium CarbonateHCID 178444450HCID 178444450, compound

Product 1

HCID 178444452HCID 178444452, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.3 g of 4-[4-(trans-4-pentylcyclohexyl)-1-butyl]phenol, 0.14 g of methyl iodide, 0.6 g of potassium carbonate and 50 ml of absolute butanone was heated to reflux overnight. Subsequently, the cooled reaction mixture was poured into water and extracted three times with 50 ml of diethyl ether each time. The combined organic phases were washed with 500 ml of water, dried over magnesium sulfate, filtered and concentrated. Chromatography of the residue on silica gel with toluene and recrystallization from ethanol gave pure 1-methoxy-4-[4-(trans-4-pentylcyclohexyl)-1-butyl]benzene with m.p. (C-I) 27° C. and cl.p. (SB -I) 16° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. customSubsequently, the cooled reaction mixture
  4. extractionextracted three times with 50 ml of diethyl ether each time
  5. washThe combined organic phases were washed with 500 ml of water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customChromatography of the residue on silica gel with toluene and recrystallization from ethanol

Sources & evidence

ORD record
ord-4cde085360454d219fcf32adb317f2aa
Source dataset
uspto-grants-1994_09
Patent number
US05346647

Reaction notes

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