| Identification | Back Directory | [Name]
2,5-di-O-allyl-1,4:3,6-dianhydro-D-glucitol | [CAS]
103536-97-6 | [Synonyms]
2,5-di-O-allyl-1,4:3,6-dianhydro 2,5-di-O-allyl-1,4:3,6-dianhydro-D-glucitol (3R,6S)-3,6-bis(allyloxy)-hexahydrofuro[3,2-b]furan D-Mannitol, 1,4:3,6-dianhydro-2,5-di-O-2-propen-1-yl- (3R,3aR,6R,6aR)-3,6-Bis(allyloxy)hexahydrofuro[3,2-b]furan | [Molecular Formula]
C12H18O4 | [MOL File]
103536-97-6.mol | [Molecular Weight]
226.27 |
| Hazard Information | Back Directory | [Synthesis]
Diallyl isosorbide ether (I) was synthesized from 3-bromo-1-propene and isosorbitol by Williamson reaction (Scheme 1). The procedure was as follows: isosorbide (3 g, 20.4 mmol) was dissolved in 50% NaOH aqueous solution (6 g, 107.2 mmol). Tetrabutylammonium bromide (TBAB, 300 mg, 0.94 mmol) at 4.5% relative to isosorbide was added to the reaction system as a phase-transfer catalyst, and allyl bromide (10 mL, 115.7 mmol) was used as an alkylation reagent. The reaction mixture was heated and stirred at 65 °C for 4 hours. After completion of the reaction, the mixture was extracted using dichloromethane. The organic phase was washed sequentially with 1 M HCl and water to remove salt impurities. The final product was purified by reduced pressure distillation (108 °C/1 torr) to obtain the pure product in 88% yield. | [References]
[1] Polymer, 2014, vol. 55, # 17, p. 4432 - 4440 [2] Patent: KR2016/111235, 2016, A. Location in patent: Paragraph 0077-0079 [3] Patent: KR101798403, 2017, B1. Location in patent: Paragraph 0123-0128 [4] Journal of the Chemical Society, 1950, p. 591,594 [5] Journal of the Chemical Society, 1947, p. 1405 |
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