Acetic Anhydride → O-Acetylsyringic Acid

HRID 1826125노트

반응식

HRID 1826125 반응식
[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]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 10742Syringic Acid

생성물 1

HCID 86760109O-Acetylsyringic Acid수율 92.5%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-da0211e55035427da6aab4e1f14fdcbd
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049311B1

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