Sucrose → HCID 57476952, compound

HRID 2281982Notes

Reaction equation

HRID 2281982 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 962WaterSolvent

Procedure

86 g of ion exchange water and 40 g (1 mole) 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. 121 g (1 mole) 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 oils were removed to obtain 700 g of a crude sucrose allyl ether aqueous solution. Hydrochloric acid was further added to adjust a pH value to 7, and the aqueous solution was then concentrated to 240 g using a rotary evaporator. Salts, such as sodium bromide and the like, which were by-products, were removed from the aqueous solution by adding 200 g of ethanol, followed by performing precipitation and filtration. Subsequently, 88 g of purified water-soluble sucrose allyl ether was obtained by distilling an excessive amount of water from the aqueous solution using a rotary evaporator. Here, the etherification degree of the water-soluble sucrose allyl ether was 2.8.

Workup

  1. temperaturewhile controlling rapid heating
  2. customcaused by an etherification reaction
  3. customthe etherification reaction
  4. customat 80° C.
  5. customfor 3 hours
  6. temperatureAfter cooling
  7. customwere removed

Sources & evidence

ORD record
ord-111d01484db64afd9abf2d2a3cfa6be0
Source dataset
uspto-grants-2015_09
Patent number
US09139671B2

Reaction notes

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