M-Cresol → 1-(Hexyloxy)-3-methylbenzene

HRID 1720164Notes

Reaction equation

HRID 1720164 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[CH:8]1[C:13]([OH:14])=[CH:12][CH:11]=[CH:10][C:9]=1[CH3:15].[OH-].[Na+]>C(O)C>[CH2:2]([O:14][C:13]1[CH:8]=[C:9]([CH3:15])[CH:10]=[CH:11][CH:12]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 342M-CresolHCID 81011-BromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 153542531-(Hexyloxy)-3-methylbenzeneYield 90.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-Bromohexane (45.0 g) is added to a solution of m-cresol (24.55 g), ethanol (500 ml) and 2N sodium hydroxide (113.5 ml), and the resulting mixture heated under reflux for 24 hours. The solution is then concentrated in vacuo and the residue extracted with ether (3×200 ml). The ether extracts are dried over magnesium sulfate, filtered, and concentrated to a dark brown oil, which is distilled in vacuo (b.p. 72° C., 0.05 mm Hg) to yield 3-n-hexyloxytoluene (39.5 g).

Workup

  1. temperaturethe resulting mixture heated
  2. temperatureunder reflux for 24 hours
  3. concentrationThe solution is then concentrated in vacuo
  4. extractionthe residue extracted with ether (3×200 ml)
  5. dry with materialThe ether extracts are dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a dark brown oil, which
  8. distillationis distilled in vacuo (b.p. 72° C., 0.05 mm Hg)

Sources & evidence

ORD record
ord-ce27ef9c998043c19e1cd8e8fd5d58b0
Source dataset
uspto-grants-1996_04
Patent number
US05504244

Reaction notes

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