Sucrose → HCID 57476952, compound

HRID 2281983Notes

Reaction equation

HRID 2281983 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].[CH2:5]([OH:27])[C@H:6]1[O:11][C@H:10]([O:12][C@:13]2([CH2:22][OH:23])[O:17][C@H:16]([CH2:18][OH:19])[C@@H:15]([OH:20])[C@@H:14]2[OH:21])[C@H:9]([OH:24])[C@@H:8]([OH:25])[C@@H:7]1[OH:26]>O>[CH2:3]=[CH:2][CH2:1][O:27][CH2:5][C@H:6]1[O:11][C@H:10]([O:12][C@:13]2([CH2:22][OH:23])[O:17][C@H:16]([CH2:18][OH:19])[C@@H:15]([OH:20])[C@@H:14]2[OH:21])[C@H:9]([OH:24])[C@@H:8]([OH:25])[C@@H:7]1[OH:26]

Participants

4

Reactant 2

HCID 5988SucroseHCID 7841Allyl bromide

Product 1

HCID 57476952HCID 57476952, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

96 g of ion exchange water and 96 g (2.4 moles) of sodium hydroxide were added to a 1 L four-necked separable flask equipped with a stirrer, a reflux condenser and a dropping funnel to dissolve the sodium hydroxide in the ion exchange water. 68.4 g (0.2 moles) of sucrose was further added, and reacted at 80° C. for 90 minutes while stirring to obtain an alkaline sucrose aqueous solution. 290 g (2.4 moles) of allyl bromide was added dropwise into the alkaline sucrose aqueous solution for 2 hours while controlling rapid heating caused by an etherification reaction. Thereafter, the etherification reaction was completed by aging the reaction solution at 80° C. for 3 hours. After cooling, 400 g of ion exchange water was added to the reaction solution taken from the separable flask, and unwanted water-soluble components were removed from the oils to obtain crude oil-soluble sucrose allyl ether. Subsequently, 250 g of ion exchange water was added, and volatile components formed as the by-products were distilled off together with water using a rotary evaporator. 120 g of n-hexane and 40 g of ion exchange water were further added, and water-soluble impurities were removed again through liquid separation. The n-hexane was distilled off from the separated oily phase using a rotary evaporator to obtain 110 g of purified oil-soluble sucrose allyl ether. The etherification degree of the oil-soluble sucrose allyl ether was 6.5.

Workup

  1. temperaturewhile controlling rapid heating
  2. customcaused by an etherification reaction
  3. customThereafter, the etherification reaction
  4. customat 80° C.
  5. customfor 3 hours
  6. temperatureAfter cooling
  7. customwere removed from the oils
  8. customto obtain crude oil-soluble sucrose allyl ether
  9. customvolatile components formed as the by-products
  10. distillationwere distilled off together with water using
  11. customa rotary evaporator
  12. addition120 g of n-hexane and 40 g of ion exchange water were further added
  13. customwater-soluble impurities were removed again through liquid separation
  14. distillationThe n-hexane was distilled off from the separated oily phase
  15. customa rotary evaporator

Sources & evidence

ORD record
ord-532a274e18f149978a5998eb45bba17c
Source dataset
uspto-grants-2015_09
Patent number
US09139671B2

Reaction notes

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