Acetic Anhydride → O-Acetylsyringic Acid

HRID 1830958ノート

反応式

HRID 1830958 の反応式
[C:1]([OH:14])(=[O:13])[C:2]1[CH:12]=[C:9]([O:10][CH3:11])[C:7]([OH:8])=[C:4]([O:5][CH3:6])[CH:3]=1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>O>[C:15]([O:13][C:1](=[O:14])[C:2]1[CH:3]=[C:4]([O:5][CH3:6])[C:7]([OH:8])=[C:9]([O:10][CH3:11])[CH:12]=1)(=[O:17])[CH3:16]

参加物

4

反応物 2

HCID 7918Acetic AnhydrideHCID 10742Syringic Acid

生成物 1

HCID 86760109O-Acetylsyringic Acid収率 92.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A suspension of syringic acid 81 (10.0 g, 50.5 mmol) in acetic anhydride (30.0 g, 27.7 mL, 294.1 mmol) was warmed gently until a clear solution was obtained. Fused sodium acetate (0.5 g, 6.10 mmol) was added to the solution which was allowed to stir for 16 hours at room temperature. The solution was poured into water (100 mL) and stirred thoroughly to ensure hydrolysis of any excess anhydride. Crude O-Acetyl-syringic acid was recrystallized from water to afford the product as an off-white powder (11.2 g, 46.7 mmol). H1 NMR (270 MHz, CDCl3) δ7.36 (s, 2H), 5.94 (br s, 1H), 3.87 (s, 6H), 2.35 (s, 3H). HRMS calcd for 240.0634, found 240.0637

後処理

  1. temperaturewas warmed gently until a clear solution
  2. customwas obtained
  3. stirringstirred thoroughly
  4. customCrude O-Acetyl-syringic acid was recrystallized from water

出典と根拠

ORDレコード
ord-296153c183c74566be1864981d95b8c3
出典データセット
uspto-grants-2006_06
特許番号
US07067511B2

反応ノート

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