Ethylene Glycol → 2-((3-Methyloxetan-3-yl)methoxy)ethanol

HRID 500289

Reaction equation

HRID 500289 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[OH-].[K+].Br[CH2:8][C:9]1([CH3:13])[CH2:12][O:11][CH2:10]1>>[CH3:8][C:9]1([CH2:13][O:3][CH2:2][CH2:1][OH:4])[CH2:12][O:11][CH2:10]1

Participants

4

Reactant 3

HCID 174Ethylene GlycolHCID 14797Potassium Hydroxide2×HCID 144860Oxetane, 3-(bromomethyl)-3-methyl-

Product 1

HCID 686765842-((3-Methyloxetan-3-yl)methoxy)ethanolYield 29.3%

Conditions

Temperature
70 °C

Procedure

Ethylene glycol (26.25 g, 0.42 mol) and KOH (19.45 g, 0.35 mol) were added to a round-bottom flask equipped with a magnetic stirrer and a reflux condenser. When all KOH had dissolved the 3-bromomethyl-3-methyloxetane (4) (46.30 g, 0.28 mol) was added. The system was heated to 70° C. for 3 hours. The reaction material was then distilled under vacuum (10 Torr) and collected as a single fraction. The distilled material was then extracted with diethyl ether and water. The water fraction was then extracted with CHCl3 multiple times to obtain 11.98 g (29.2% yield) of the final product, though analysis of the water phase indicated a significant amount of HE 1Ox was unextracted. H1 NMR (CDCl3): δ 1.31 ppm (—CH3, 3H, s), δ 2.63 ppm (—OH, 1H, t), δ 3.54 ppm (—CH2—, 2H, s), δ 3.60 ppm (—OCH2—, 2H, t), δ 3.76 ppm (HOCH2—, 2H, q), δ 4.38 ppm (oxetane CH2, 2H, d), δ 4.55 ppm (oxetane CH2, 2H, d).

Workup

  1. customequipped with a magnetic stirrer and a reflux condenser
  2. additionwas added
  3. distillationThe reaction material was then distilled under vacuum (10 Torr)
  4. customcollected as a single fraction
  5. extractionThe distilled material was then extracted with diethyl ether and water
  6. extractionThe water fraction was then extracted with CHCl3 multiple times

Sources & evidence

ORD record
ord-a8e76e7dbf694ab69c38c7c4edaab860
Source dataset
uspto-grants-2010_08
Patent number
US07771825B2

Linked notes

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