Catechol → 2-(Hexyloxy)phenol

HRID 2120020Notes

Reaction equation

HRID 2120020 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C(O)C>ClCCl>[CH2:16]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 289CatecholHCID 702EthanolHCID 81011-BromohexaneHCID 11430Potassium Carbonate

Product 1

HCID 124137162-(Hexyloxy)phenolYield 29%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Catechol (35.0 g, 0.32 mol), potassium carbonate (109.0 g, 0.79 mol) and 1-bromohexane (52.5 g, 0.32 mol) were added to ethanol (300 ml) and heated under reflux for 48 h. After cooling, dichloromethane (300 ml) was added and the solid residues removed by filtration. The solvents were then removed in vacuo and the crude product was purified by column chromatography on silica gel to give title compound (17.9 g, 29%) as a colourless liquid. Found: C, 73.90; H, 9.20. C12H18O2 requires C, 74.19; H, 9.34. δH (CHCl3) 6.95-6.83 (m, 4H, ArH), 5.66 (s, 1H, OH), 4.04 (t, J 7, 2H, ArOCH2), 1.89-1.79 (m, 2H, ArOCH2CH), 1.55-1.35 (m, 6H, CH2), 0.95 (t, J 7, 3H, CH2CH3). MS (FAB), 194 (M+, 100%), 110 (45%), 95 (7%), 83 (12%), 69 (9%), 55 (18%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 48 h
  3. temperatureAfter cooling
  4. customthe solid residues removed by filtration
  5. customThe solvents were then removed in vacuo
  6. customthe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c3210f72959f494391401780151dee84
Source dataset
uspto-grants-2004_02
Patent number
US06689290B2

Reaction notes

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