Allyl Alcohol → 6-[(2-Propen-1-yloxy)methyl]-1,4-dioxane-2-methanol

HRID 1278020Notes

Reaction equation

HRID 1278020 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[Na].[O:6]([CH2:11][CH:12]1[CH2:14][O:13]1)[CH2:7][CH:8]1[CH2:10][O:9]1>O>[CH2:1]([O:4][CH2:14][CH:12]1[O:13][CH:8]([CH2:10][OH:9])[CH2:7][O:6][CH2:11]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 16704Diglycidyl etherHCID 5360545Sodium

Product 1

HCID 128887526-[(2-Propen-1-yloxy)methyl]-1,4-dioxane-2-methanolYield 18%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

136 ml of allyl alcohol (2.0 mole, Aldrich) is stirred under nitrogen at room temperature and 0.25 g of sodium is added to the mixture and stirring continued for 2.5 hours. Then 13.1 g of 2,2'-(oxybismethylene)bisoxirane (0.1 mole) is added and the mixture then heated at reflux for 18 hours. The mixture is then cooled to room temperature and with stirring is poured into 350 ml of water. The aqueous mixture is extracted with 2×200 ml portions of chloroform, the CHCl3 extracts are combined and dried over anhydrous sodium sulfate. The CHCl3 is removed in vacuo and the resulting yellow oil then vacuum distilled through a 10 cm vigreux column. The fraction distilling at 120°-123° @ 0.4 mm is collected yielding 3.2 g (18%) of the above compound.

Workup

  1. temperaturethe mixture then heated
  2. temperatureat reflux for 18 hours
  3. stirringwith stirring
  4. extractionThe aqueous mixture is extracted with 2×200 ml portions of chloroform
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe CHCl3 is removed in vacuo
  7. distillationthe resulting yellow oil then vacuum distilled through a 10 cm vigreux column
  8. distillationThe fraction distilling at 120°-123° @ 0.4 mm
  9. customis collected

Sources & evidence

ORD record
ord-07db6c3ba45c47d89bee7057e3e57f8d
Source dataset
uspto-grants-1981_07
Patent number
US04279902

Reaction notes

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