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

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Reaction Steps

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.

Provenance & Evidence