Allyl Alcohol → Tetrahydro-5-[(2-propenyloxy)methyl]-2-furanmethanol

HRID 1278022

Reaction equation

HRID 1278022 reaction equation
[CH2:1]([OH:4])[CH:2]=[CH2:3].[Na].[CH2:6]1[O:8][CH:7]1[CH2:9][CH2:10][CH:11]1[O:13][CH2:12]1>O>[CH2:1]([O:4][CH2:12][CH:11]1[O:13][CH:7]([CH2:6][OH:8])[CH2:9][CH2:10]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 159031,2:5,6-DiepoxyhexaneHCID 5360545Sodium

Product 1

HCID 12888746Tetrahydro-5-[(2-propenyloxy)methyl]-2-furanmethanolYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

100 ml of allyl alcohol (1.47 mole, Aldrich) is cooled to 5° in an ice-bath and under a nitrogen atmosphere 0.3 g of sodium (0.013 mole, washed with hexane to remove the mineral oil) is slowly added to the rapidly stirred mixture. The addition of the sodium is made at such a rate that the temperature remains below 20°. After the addition of the sodium has been completed, the mixture is allowed to stir for 1/2 hour and slowly warmed to room temperature. Slowly, with stirring 15.0 g of 1,5-hexadiene diepoxide (0.131 mole) is added to the mixture. After the addition of the diepoxide has been completed, the reaction mixture is heated at reflux for 16 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 distilling column. The fraction distilling at 108°-110° @ 0.5 mm is collected yielding 14.65 g (65%) of the above compound.

Workup

  1. washwashed with hexane
  2. customto remove the mineral oil)
  3. additionis slowly added to the rapidly stirred mixture
  4. additionThe addition of the sodium
  5. customremains below 20°
  6. additionAfter the addition of the sodium
  7. additionis added to the mixture
  8. additionAfter the addition of the diepoxide
  9. temperaturethe reaction mixture is heated
  10. temperatureat reflux for 16 hours
  11. temperatureThe mixture is then cooled to room temperature
  12. stirringwith stirring
  13. extractionThe aqueous mixture is extracted with 2×200 ml portions of chloroform
  14. dry with materialdried over anhydrous sodium sulfate
  15. customThe CHCl3 is removed in vacuo
  16. distillationthe resulting yellow oil then vacuum distilled through a 10 cm
  17. distillationvigreux distilling column
  18. distillationThe fraction distilling at 108°-110° @ 0.5 mm
  19. customis collected

Sources & evidence

ORD record
ord-58e21e856cd14f11a78a7778fb9787e8
Source dataset
uspto-grants-1981_07
Patent number
US04279902

Linked notes

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