Acetic Anhydride → O-Acetylsyringic Acid

HRID 1826125ノート

反応式

HRID 1826125 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) δ 7.36 (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-da0211e55035427da6aab4e1f14fdcbd
出典データセット
uspto-grants-2006_05
特許番号
US07049311B1

反応ノート

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