9-Anthracenecarboxylic acid → Anthracene-9-carbonyl chloride

HRID 489888

반응식

HRID 489888 반응식
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]([OH:17])=O)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C(Cl)(Cl)[Cl:19]>S(Cl)(Cl)=O>[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[C:15]([Cl:19])=[O:17])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 2

HCID 22019-Anthracenecarboxylic acidHCID 6212Chloroform

생성물 1

HCID 167528Anthracene-9-carbonyl chloride수율 59%

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

실험 절차

Anthracene-9-carboxylic acid (recrystallized from ethanol, 12.05 g, 54.3 mmol) was suspended in a mixture of chloroform (60 mL, Aldrich, amylenes-stabilized) and thionyl chloride (12 mL) and heated under reflux until a clear solution was obtained (about 30 minutes). The solvent was removed by distillation under reduced pressure and the residual hot oil was dissolved in toluene (20 mL) and hexane (100 mL) was added. After cooling to ambient temperature the crystalline product was collected by filtration and dried in a stream of nitrogen then under high vacuum to give the title compound as a yellow solid (7.69 g, 59%). Non-commercially available carboxylic acids referred to in this section were prepared as described below. If desired they were converted to the corresponding carbonyl chloride using thionyl chloride as described above.

후처리

  1. temperatureheated
  2. temperatureunder reflux until a clear solution
  3. customwas obtained (about 30 minutes)
  4. customThe solvent was removed by distillation under reduced pressure
  5. dissolutionthe residual hot oil was dissolved in toluene (20 mL)
  6. additionhexane (100 mL) was added
  7. filtrationwas collected by filtration
  8. customdried in a stream of nitrogen

출처 및 근거

ORD 기록
ord-6d6df2e26fae423f9920d14f54d9331b
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06979741B2

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