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

HRID 889481ノート

反応式

HRID 889481 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-650bfd3b5b7540aaba914637203547b6
出典データセット
uspto-grants-2012_08
特許番号
US08252833B2

反応ノート

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