Hydrogen Bromide → Heptaacetate bromide

HRID 27585

Reaction equation

HRID 27585 reaction equation
[OH:1][CH:2]1[O:10][C@H](CO)[C@@H](O)[C@H](O)[C@H:3]1O.C(Cl)Cl.[BrH:16]>C(O)(=O)C>[Br-:16].[C:2]([O-:10])(=[O:1])[CH3:3].[C:2]([O-:10])(=[O:1])[CH3:3].[C:2]([O-:10])(=[O:1])[CH3:3].[C:2]([O-:10])(=[O:1])[CH3:3].[C:2]([O-:10])(=[O:1])[CH3:3].[C:2]([O-:10])(=[O:1])[CH3:3].[C:2]([O-:10])(=[O:1])[CH3:3]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 5793D-GlucoseHCID 6344Dichloromethane2×

Product 1

HCID 86737203Heptaacetate bromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Glc 1β,4 glc is converted to its octaacetate form by conventional methods as disclosed in Methods of Carbohydrate Chemistry 1, 334. A 20 g. portion of this octaacetate is dissolved in 200 ml. of methylene chloride and the solution is cooled to 0° C. An 80 ml. portion of 32% hydrobromic acid in glacial acetic acid is added and the mixture is allowed to stand in an ice bath for 2 hours. The mixture is then poured into crushed ice and diluted with 200 ml. of methylene chloride. The organic layer is separated, washed repeatedly with ice water until neutral, dried over anhydrous sodium sulfate and evaporated in vacuo, giving glc 1β,4 glc heptaacetate bromide as a white solid.

Workup

  1. additionThe mixture is then poured
  2. custominto crushed ice
  3. additiondiluted with 200 ml
  4. customThe organic layer is separated
  5. washwashed repeatedly with ice water until neutral,
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-6a50caf659d14d7391d1c254f7af3fa4
Source dataset
uspto-grants-1980_09
Patent number
US04221907

Linked notes

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