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

HRID 1175260Notes

Reaction equation

HRID 1175260 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-699bf9871dc241ef96d34706b3125a3e
Source dataset
uspto-grants-2010_11
Patent number
US07838499B2

Reaction notes

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