Malonic Acid → 10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic acid

HRID 258201

반응식

HRID 258201 반응식
[CH2:1]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9](O)[C:8]2[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:2]1.C(O)(=O)[CH2:18][C:19]([OH:21])=[O:20]>>[CH:4]1[C:3]2[CH2:2][CH2:1][C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[CH:9]([CH2:18][C:19]([OH:21])=[O:20])[C:8]=2[CH:7]=[CH:6][CH:5]=1

참가 물질

3

반응물 2

HCID 867Malonic AcidHCID 14588Dibenzosuberol

생성물 1

HCID 1266909110,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylacetic acid

반응 조건

온도
160 °C

실험 절차

A round-bottom flask, equipped with a distillation apparatus, is charged with dibenzosuberol (25.0 g, 0.119 mol) and malonic acid (61.9 g, 0.595 mol). The mixture is heated in an 160° C. oil bath. The solids melt. Gas bubbles form and water and acetic acid are distilled through the condenser. After 30 minutes, the mixture is cooled to room temperature and dissolved in ethyl acetate. The organic solution is washed with brine and dried (magnesium sulfate). The solvent is removed in vacuo to give an off white solid, which is recrystallized from hexane-ethyl acetate/1:1 to yield the title compound as white crystals, 28.8 g; mp 164°-165° C.

후처리

  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 (magnesium sulfate)
  7. customThe solvent is removed in vacuo
  8. customto give an off white solid, which
  9. customis recrystallized from hexane-ethyl acetate/1:1

출처 및 근거

ORD 기록
ord-67075623cdb94f95b22545428d5c9080
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264577

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