Hydrochloric Acid → 2-(Dibenzothiophene-2-ylcarbonyl)benzoic acid

HRID 68180

반응식

HRID 68180 반응식
[Cl-].[Al+3].[Cl-].[Cl-].[C:5]1(=[O:15])[O:10][C:8](=[O:9])[C:7]2=[CH:11][CH:12]=[CH:13][CH:14]=[C:6]12.[CH:16]1[C:24]2[C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[S:21][C:20]=2[CH:19]=[CH:18][CH:17]=1.Cl>ClCCl.O>[C:8]([C:7]1[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=1[C:5]([C:26]1[CH:27]=[CH:28][C:22]2[S:21][C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:24]=3[C:23]=2[CH:25]=1)=[O:15])([OH:10])=[O:9]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 3023DibenzothiopheneHCID 6811Phthalic AnhydrideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 43467782-(Dibenzothiophene-2-ylcarbonyl)benzoic acid수율 107.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

반응 조건

온도
5 °C

실험 절차

To a mixture of aluminum chloride (40.0 g, 300 mmol) in anhydrous dichloromethane (1000 cm3) is added a suspension of phthalic anhydride (14.8 g, 100 mmol) in anhydrous dichloromethane (200 cm3). The suspension is stirred for 30 minutes, cooled to 5° C. and then a solution of dibenzothiophene (20.0 g, 110 mmol) in anhydrous dichloromethane (200 cm3) added drop wise under cooling with ice. After addition, the mixture is allowed to stir at 23° C. for 4 hours. The reaction mixture poured into a solution of water (1000 cm3) and concentrated hydrochloric acid (400 cm3). The product extracted with dichloromethane (2 200 cm3) and the organic extracted with aqueous sodium hydroxide (5%, 500 cm3). The basic layer acidified and the oily precipitate is isolated by decanting away the acidic solution. Water (200 cm3) is added, which solidified the oil and the solid collected by filtration, washed with water (500 cm3) and dried under vacuum to give 2-(o-carboxybenzoyl)dibenzothiophene as a pale yellow solid (35.64 g, 99%). 1H NMR (300 MHz, CDCl3) 8.47-8.52 (m, 1H), 7.99-8.15 (m, 2H), 7.60-7.86 (m, 4H), 7.35-7.57 (m, 4H).

후처리

  1. additionis added
  2. temperatureunder cooling with ice
  3. additionAfter addition
  4. stirringto stir at 23° C. for 4 hours
  5. extractionThe product extracted with dichloromethane (2 200 cm3)
  6. extractionthe organic extracted with aqueous sodium hydroxide (5%, 500 cm3)
  7. customthe oily precipitate is isolated
  8. customby decanting away the acidic solution
  9. additionWater (200 cm3) is added
  10. filtrationthe solid collected by filtration
  11. washwashed with water (500 cm3)
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-ec4ae702de5a4386be568b0b629a7a38
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08821762B2

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