ChemicalBook--->CAS DataBase List--->103536-97-6

103536-97-6

103536-97-6 Structure

103536-97-6 Structure
IdentificationBack 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
Chemical PropertiesBack Directory
[Boiling point ]

173 °C(Press: 10 Torr)
[density ]

1.09±0.1 g/cm3(Predicted)
[storage temp. ]

2-8°C
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302-H315-H319-H335
[Precautionary statements ]

P261-P305+P351+P338
Hazard InformationBack Directory
[Synthesis]

Allyl bromide

106-95-6

Isosorbide

652-67-5

3,6-bis(allyloxy)hexahydrofuro[3,2-b]furan

6338-34-7

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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