Hydrogen Bromide → Diacetone L-sorbose

HRID 1462583Notes

Reaction equation

HRID 1462583 reaction equation
[OH:1][CH2:2][C:3]([C@H:5]([C@@H:7]([C@H:9]([CH2:11][OH:12])[OH:10])[OH:8])[OH:6])=[O:4].Br>CC(C)=O>[CH3:2][C:3]1([CH3:5])[O:6][C@H:5]2[C@@H:7]3[O:8][C:9]([CH3:11])([CH3:7])[O:10][C@:9]3([CH2:11][OH:12])[O:4][C@H:3]2[CH2:2][O:1]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 6904L-(-)-Sorbose

Product 1

HCID 11043496Diacetone L-sorboseYield 152.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To 200 ml of acetone were added 10.0 g of L-sorbose, 143 mg of cuprous oxide and 173 mg of 47% hydrobromic acid, and the mixture was refluxed in a warm-water bath at 60° C. for 8 hours. The refluxing solvent was continuously dried with 20 g of molecular sieves 3A which was placed between the reaction vessel and the cooling tube. After the conclusion of the reaction, the same post-treatment as in Example 5 was carried out, thus giving 11.0 g (76.2%) of 2,3:4,6-di-O-isopropylidene-L-sorbofuranose.

Workup

  1. temperaturethe mixture was refluxed in
  2. dry with materialThe refluxing solvent was continuously dried with 20 g of molecular sieves 3A which
  3. customAfter the conclusion of the reaction

Sources & evidence

ORD record
ord-a167d522cdb949d3a16b23eca94a0f03
Source dataset
uspto-grants-1984_07
Patent number
US04460767

Reaction notes

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