Catechol → 2-(Hexyloxy)phenol

HRID 1442476Notes

Reaction equation

HRID 1442476 reaction equation
[C:1]1([C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4])[OH:2].Br[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[CH2:10]([O:2][C:1]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[OH:4])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 289CatecholHCID 81011-BromohexaneHCID 11430Potassium Carbonate

Product 1

HCID 124137162-(Hexyloxy)phenolYield 47,696.801%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture consisting of 740 mL of methyl ethyl ketone, 120 g (1.09 mol) of catechol, 178 g (1.09 mmol) of 1-bromohexane and 211 g (1.53 mol, 1.4 eq.) of potassium carbonate was refluxed for 25 hours. After cooling, the mixture was filtered followed by distilling off the solvent. 202 g of residue was purified by silica gel column chromatography followed by distillation to obtain 101 g of a clear liquid.

Workup

  1. temperaturewas refluxed for 25 hours
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. distillationby distilling off the solvent
  5. custom202 g of residue was purified by silica gel column chromatography
  6. distillationfollowed by distillation

Sources & evidence

ORD record
ord-aeb7faf42c2d476bb639f77383a05b57
Source dataset
uspto-grants-2010_02
Patent number
US07658979B2

Reaction notes

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