Thionyl Chloride → 4,9-Bis(propyloxy)naphtho[2,3-c]furan-1,3-dione

HRID 889481노트

반응식

HRID 889481 반응식
[CH2:1]([O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([O:15][CH2:16][CH2:17][CH3:18])=[C:7]([C:19]([OH:21])=[O:20])[C:6]=1[C:22]([OH:24])=O)[CH2:2][CH3:3].S(Cl)(Cl)=O>C(Cl)(Cl)Cl>[CH2:1]([O:4][C:5]1[C:6]2[C:22](=[O:24])[O:20][C:19](=[O:21])[C:7]=2[C:8]([O:15][CH2:16][CH2:17][CH3:18])=[C:9]2[C:14]=1[CH:13]=[CH:12][CH:11]=[CH:10]2)[CH2:2][CH3:3]

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 210793301,4-Bis(propyloxy)-2,3-naphthalenedicarboxylic acid

생성물 1

HCID 580176444,9-Bis(propyloxy)naphtho[2,3-c]furan-1,3-dione수율 103.7%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
65 °C

실험 절차

1,4-Bis(propyloxy)-2,3-naphthalenedicarboxylic acid (8.91 g, 26.8 mmol) was suspended in chloroform (80 ml) and thionyl chloride (20.5 ml, 281.4 mmol) was added dropwise whilst monitoring the temperature (no significant change). The reaction was heated at 65° C. for 2.5 hours. The reaction mixture was cooled to room temperature and concentrated in vacuo. The yellow/brown solid was azeotroped with chloroform (×3) to afford the title compound as a beige solid (8.74 g, 27.8 mmol).

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customThe yellow/brown solid was azeotroped with chloroform (×3)

출처 및 근거

ORD 기록
ord-650bfd3b5b7540aaba914637203547b6
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08252833B2

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