Hydrogen Bromide → Heptaacetate bromide

HRID 224479

Reaction equation

HRID 224479 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 in 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-68f0f92c196f49ada6b8e9f4caf4dc85
Source dataset
uspto-grants-1980_11
Patent number
US04232150

Linked notes

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