Acetic Anhydride → 6,8-dimethoxyisochroman-1,3-dione

HRID 432945노트

반응식

HRID 432945 반응식
[C:1]([CH2:4][C:5]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[C:6]=1[C:7]([OH:9])=[O:8])(O)=[O:2].C(OC(=O)C)(=O)C>C1(C)C=CC=CC=1>[CH3:15][O:14][C:12]1[CH:13]=[C:5]2[C:6](=[C:10]([O:16][CH3:17])[CH:11]=1)[C:7](=[O:9])[O:8][C:1](=[O:2])[CH2:4]2

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 41666252-(carboxymethyl)-4,6-dimethoxybenzoic acid

생성물 1

HCID 118168976,8-dimethoxyisochroman-1,3-dione수율 83.1%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
110 °C

실험 절차

2-Carboxymethyl-4,6-dimethoxybenzoic acid (60) (3.97 gm) was stirred in toluene (40.0 mL) at ambient temperature in a 100 mL flask with magnetic stirring. Acetic anhydride (1.72 mL) was added and the mixture heated to 110° C. Monitoring by HPLC revealed that the reaction was complete within 2.5 hours. Heat was then removed. Crystallization of 6,8-dimethoxyisochroman-1,3-dione (25) occurred as the solution cooled. The mixture was cooled to 2° C. After a short hold time, yellow crystalline solids were filtered, washed with fresh toluene and then dried on high vacuum. 6,8-Dimethoxyisochroman-1,3-dione (25) (3.05 g) was isolated as a yellow crystalline solid.

후처리

  1. temperatureHeat
  2. customwas then removed
  3. customCrystallization of 6,8-dimethoxyisochroman-1,3-dione (25)
  4. temperaturecooled
  5. temperatureThe mixture was cooled to 2° C
  6. filtrationAfter a short hold time, yellow crystalline solids were filtered
  7. washwashed with fresh toluene
  8. customdried on high vacuum

출처 및 근거

ORD 기록
ord-847e912df363482db53662f3d2be951e
출처 데이터셋
uspto-grants-2003_12
특허 번호
US06664401B2

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