Ethylene Glycol → 2-(Cyclohex-2-enyloxy)ethanol

HRID 425071

Reaction equation

HRID 425071 reaction equation
Br[CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1.[CH2:8]([OH:11])[CH2:9][OH:10].C([O-])([O-])=O.[Cs+].[Cs+].CC(=O)OCC>CN(C=O)C.O>[CH:2]1([O:10][CH2:9][CH2:8][OH:11])[CH2:7][CH2:6][CH2:5][CH:4]=[CH:3]1

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 1370573-Bromocyclohexene

Product 1

HCID 112865262-(Cyclohex-2-enyloxy)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 3-bromocyclohex-1-ene (0.5 g) in anhydrous DMF (5 mL) were added ethylene glycol (3 eq) and Cs2CO3 (5 g). The mixture was heated to 80° C. and stirred overnight, after which TLC (PE:EA=20:1) showed the reaction was complete. Then the mixture was poured into water and extracted with EA, washed with water and brine, and concentrated to an oil, which was purified by column chromatography to obtain intermediate BU (0.3 g).

Workup

  1. extractionextracted with EA
  2. washwashed with water and brine
  3. concentrationconcentrated to an oil, which
  4. customwas purified by column chromatography
  5. customto obtain intermediate BU (0.3 g)

Sources & evidence

ORD record
ord-9d804a9ad69248d581b0a1e20095d460
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Linked notes

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