Malonic Acid → 5H-Dibenzo(A,D)cyclohepten-5-ylacetic acid

HRID 1769558ノート

反応式

HRID 1769558 の反応式
[CH:1]1[CH:15]=[C:14]2[C:4]([CH:5](O)[C:6]3[C:11]([CH:12]=[CH:13]2)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:3][CH:2]=1.C(O)(=O)[CH2:18][C:19]([OH:21])=[O:20]>>[CH:15]1[C:14]2[CH:13]=[CH:12][C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH:5]([CH2:18][C:19]([OH:21])=[O:20])[C:4]=2[CH:3]=[CH:2][CH:1]=1

参加物

3

反応物 2

HCID 867Malonic AcidHCID 82577Dibenzosuberenol

生成物 1

HCID 38305635H-Dibenzo(A,D)cyclohepten-5-ylacetic acid

反応条件

温度
160 °C

実験手順

A round-bottom flask, equipped with a distillation apparatus, is charged with dibenzosuberenol (10.0 g, 48.01 mmol) and malonic acid (25.0 g, 240.08 mmol). The mixture is heated in a 160° C. oil bath. The solids melt. Gas bubbles form and water and acetic acid are distilled through the condenser. After 1.5 hours, the mixture is cooled to room temperature and dissolved in ethyl acetate. The organic solution is washed with brine and dried over MgSO4. The solvent is removed in vacuo to give an off-white solid, which is recrystallized from hexane-ethyl acetate- (AcOEt)/1:1 to yield the title compound as white crystals, 10.2 g; mp 167°-168° C.

後処理

  1. customA round-bottom flask, equipped with a distillation apparatus
  2. distillationGas bubbles form and water and acetic acid are distilled through the condenser
  3. temperaturethe mixture is cooled to room temperature
  4. dissolutiondissolved in ethyl acetate
  5. washThe organic solution is washed with brine
  6. dry with materialdried over MgSO4
  7. customThe solvent is removed in vacuo
  8. customto give an off-white solid, which
  9. customis recrystallized from hexane-ethyl acetate- (AcOEt)/1

出典と根拠

ORDレコード
ord-3cd56b99b344409aa53154fed448e538
出典データセット
uspto-grants-1995_01
特許番号
US05380925

反応ノート

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