반응 #1766191

반응 방정식

benzyl chloride

hydrogen

2-(2-furyl)-5-hydroxy-1,3-dioxane

sodium hydride

→

amber oil

수율 86.5%

5-benzyloxy-2-(2-furyl)-1,3-dioxane

수율 86.5%

용매

toluene

반응 조건

후처리

1. 1
   온도maintained
2. 2
   workup.WAITfor ca. 21 hours
3. 3
   온도to cool to room temperature
4. 4
   workup.WAITremain at that temperature for 4 days
5. 5
   세척The mixture was washed with two 250-ml volumes of water, which aqueous washes
6. 6
   추출extracted with toluene (three 150-ml volumes)
7. 7
   기타to recover product
8. 8
   기타The toluene solution was combined with the washed reaction mixture
9. 9
   건조the total mixture was dried over magnesium sulfate
10. 10
    여과filtered
11. 11
    기타evaporated under reduced pressure

실험 절차

To a stirred solution of 17 g of 2-(2-furyl)-5-hydroxy-1,3-dioxane in 150 ml of toluene was added over a period of twenty minutes 4.4 g of sodium hydride (54.7% in mineral oil). The mixture was allowed to stir for 1 hour to permit evolution of by-product hydrogen, after which time 12.7 g of benzyl chloride was added during 15 minutes. The reaction mixture was heated to 70° C and maintained thereat for ca. 21 hours. The reaction mixture was allowed to cool to room temperature and remain at that temperature for 4 days. The mixture was washed with two 250-ml volumes of water, which aqueous washes were combined and extracted with toluene (three 150-ml volumes) to recover product. The toluene solution was combined with the washed reaction mixture and the total mixture was dried over magnesium sulfate, filtered and evaporated under reduced pressure to give 22.5 g of amber oil. The oil was washed with 25 ml of hexane, which procedure produced 17.5 g of clear oil. The clear oil was distilled and those fractions boiling at a bath temperature of 144°-154° C under 2 × 10-4 mm Hg (bath temp. 144°-147°; nD25 1.5349: bath temp. 148°-154°; nD25 1.5379) were combined (10.6 g) and a portion was submitted for elemental analysis. Upon refrigeration for ca. 48 hours, 0.5 g of crystalline 5-benzyloxy-2-(2-furyl)-1,3-dioxane precipitated, m.p. 58.5°-61° C.

출처