Catechol → 2-(Hexyloxy)phenol
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
Product 1
Reagents, catalysts & solvents 1
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
- temperaturewas refluxed for 25 hours
- temperatureAfter cooling
- filtrationthe mixture was filtered
- distillationby distilling off the solvent
- custom202 g of residue was purified by silica gel column chromatography
- distillationfollowed by distillation
Sources & evidence
- ORD record
- ord-aeb7faf42c2d476bb639f77383a05b57
- Source dataset
- uspto-grants-2010_02
- Patent number
- US07658979B2
Reaction notes
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