Acetone → HCID 12813111, compound

HRID 1447663Notes

Reaction equation

HRID 1447663 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:13]2[CH2:23][O:24][C@H:11]([O:12]2)[C@@H:10]1[O:25]C1CCCCO1)C1C=CC=CC=1.Cl.[OH-:33].[Na+].[CH3:35][C:36]([CH3:38])=O>>[C:35]([O:12][C@@H:13]1[C@@H:14]([O:15][CH2:16][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C@H:9]([O:8][CH2:1][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:10]2[CH2:11][O:24][C@@H:23]1[O:25]2)(=[O:33])[C:36]1[CH:38]=[CH:11][CH:10]=[CH:9][CH:14]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 12813134HCID 12813134, compound

Product 1

HCID 12813111HCID 12813111, compound

Procedure

A solution of 51 g of 1,6-anhydro-3,4-di-O-benzyl-2-O-tetrahydropyranyl-β-D-glucopyranose in 400 ml of acetone is warmed with 20 ml 1 N hydrochloric acid to 50° for 20 minutes. After cooling, this solution is neutralised with 1 N sodium hydroxide solution and evaporated to dryness. The residue is taken up in ether, this solution is washed thoroughly with water and dried over magnesium sulphate and the solvent is evaporated. The product is benzoylated as described in Example 3 and the 1,6-anhydro-2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranose which is thus obtained is purified by recrystallisation.

Workup

  1. temperatureAfter cooling
  2. customevaporated to dryness
  3. washthis solution is washed thoroughly with water
  4. dry with materialdried over magnesium sulphate
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-cb56844ec5d7429f85926690087a7e57
Source dataset
uspto-grants-1979_12
Patent number
US04177344

Reaction notes

Loading…