Potassium Carbonate → 2-[2-(Cyclopropylmethoxy)phenoxy]ethan-1-OL

HRID 1648388

Reaction equation

HRID 1648388 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][OH:11].[CH:12]1([CH2:15]Br)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:12]1([CH2:15][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8][CH2:9][CH2:10][OH:11])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 785192-(2-Hydroxyethoxy)phenolHCID 81503Bromomethylcyclopropane

Product 1

HCID 199199282-[2-(Cyclopropylmethoxy)phenoxy]ethan-1-OLYield 114.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Hydroxy-1-(2-hydroxyethyloxy)benzene (4 g, 26.0 mmol), cyclopropylmethyl-bromide (5.0 g, 37.0 mmol), and potassium carbonate (5.0 g, 36.2 mmol) were combined in acetone (80 mL) and the mixture was refluxed for 18 hours. The mixture was cooled and filtered. The filtrate was evaporated and the residue was dissolved in ether. The solution was washed with water 2N sodium hydroxide, and then brine, and dried over magnesium sulfate. Evaporation gave 2-cyclopropylmethyloxy-1-(2-hydroxyethyloxy)benzene (6.2 g) as an oil.

Workup

  1. temperaturethe mixture was refluxed for 18 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated
  5. dissolutionthe residue was dissolved in ether
  6. washThe solution was washed with water 2N sodium hydroxide
  7. dry with materialbrine, and dried over magnesium sulfate
  8. customEvaporation

Sources & evidence

ORD record
ord-b36ddcb32ab947d8a48b447404b689d7
Source dataset
uspto-grants-1995_07
Patent number
US05436264

Linked notes

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