Resorcinol → 3-(Pentyloxy)phenol

HRID 439752Notes

Reaction equation

HRID 439752 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[C:7]1([CH:14]=[CH:13][CH:12]=[C:10]([OH:11])[CH:9]=1)[OH:8].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:2]([O:8][C:7]1[CH:9]=[C:10]([OH:11])[CH:12]=[CH:13][CH:14]=1)[CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 5054ResorcinolHCID 80571-BromopentaneHCID 11430Potassium Carbonate

Product 1

HCID 156922293-(Pentyloxy)phenol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 24.8 ml of 1-Bromopentane, 66.0 g of resorcinol, and 41.5 g of potassium carbonate is stirred in 400 ml of anhydrous dimethylformamide at 60° C. for 17 hours. This mixture is filtered through Celite and concentrated under vacuum. The residue is taken up in water and extracted 3 times with ether. The combined extracts are washed with saturated sodium chloride, dried over magnesium sulfate, filtered, and concentrated under vacuum. The residue is flash chromatographed on normal phase silica gel eluting with a 4:1 ratio of hexane:ether to yield 3-pentyloxyphenol as a clear oil.

Workup

  1. filtrationThis mixture is filtered through Celite
  2. concentrationconcentrated under vacuum
  3. extractionextracted 3 times with ether
  4. washThe combined extracts are washed with saturated sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customchromatographed on normal phase silica gel eluting with a 4:1 ratio of hexane

Sources & evidence

ORD record
ord-d9f447986c83435eb66b73a360740f3d
Source dataset
uspto-grants-1996_05
Patent number
US05516767

Reaction notes

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