Sulfuric Acid → Diacetone-D-glucose

HRID 843209

反応式

HRID 843209 の反応式
S(=O)(=O)(O)O.[OH:6][C@H:7]1[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]1[OH:9].[OH-].[Na+]>CC(C)=O>[CH3:7][C:8]1([CH3:10])[O:13][C@@H:12]([C@H:14]2[O:15][C@@H:7]3[O:6][C:14]([CH3:16])([CH3:12])[O:9][C@@H:8]3[C@H:16]2[OH:17])[CH2:10][O:11]1

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 79025Alpha-D-Glucose

生成物 1

HCID 7067560Diacetone-D-glucose収率 112.5%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Sulfuric acid (40 ml) is added dropwise to a solution of α-D-glucose (41) (50 g, 0,28 mol) in acetone (1 l) at 0° C. The reaction mixture is stirred for 24 h and then it is neutralized using sodium hydroxide (6 M). The acetone is evaporated and the aqueous layer is extracted with chloroform (X2). The chloroform is dried (MgSO4) filtered and evaporated. Crystallization from cyclohexane yielded the di-isopropylidene glucose (42) (41 g, 57%).

後処理

  1. customThe acetone is evaporated
  2. extractionthe aqueous layer is extracted with chloroform (X2)
  3. dry with materialThe chloroform is dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customCrystallization from cyclohexane

出典と根拠

ORDレコード
ord-80b91a09cd0a4ad6b1d6e94c624dd2c4
出典データセット
uspto-grants-2002_04
特許番号
US06376657B1

関連ノート

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