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

HRID 2038503Notes

Reaction equation

HRID 2038503 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-0cbd6120d65d47f1972fe53c9afa3ded
Source dataset
uspto-grants-2013_11
Patent number
US08575321B2

Reaction notes

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