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p-Toluenesulfonic acid monohydrate → 1,2-Dimethyl-3-(prop-2-en-1-yl)benzene

HRID 2167229
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HRID 2167229 반응식
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9](O)([CH3:11])C.O.[C:14]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:9][CH:11]=[CH2:14])[C:2]=1[CH3:1]
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참가 물질

4

반응물 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 235905312-(2,3-Dimethylphenyl)propan-2-ol

생성물 1

HCID 206267321,2-Dimethyl-3-(prop-2-en-1-yl)benzene수율 92%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

2-(2,3-Dimethylphenyl)propan-2-ol, compound of formula (XXIV), prepared according to either example 1 or example 2, (1.10 g, 6.70 mmol), was dissolved in benzene (20 mL), and p-toluenesulfonic acid monohydrate (35 mg, 0.18 mmol) was added. The mixture was stirred at room temperature for 3 h. Silica gel (200 mg) was added, and stirring was continued for ca. 16 hours, and then the reaction mixture was refluxed for 30 min. After cooling to room temperature, the mixture was filtered, washed with aqueous K2CO3 solution, conventionally dried, and concentrated under reduced pressure, to yield 0.90 g (92%) of the title compound. 1H NMR: 2.02 (m, 3H), 2.21 (s, 3H), 2.28 (s, 3H), 4.82 (m, 1H), 5.17 (m, 1H), 6.97 (m, 1H), 7.05 (m, 2H).

후처리

  1. additionSilica gel (200 mg) was added
  2. stirringstirring
  3. waitwas continued for ca. 16 hours
  4. temperaturethe reaction mixture was refluxed for 30 min
  5. temperatureAfter cooling to room temperature
  6. filtrationthe mixture was filtered
  7. washwashed with aqueous K2CO3 solution
  8. customconventionally dried
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-6931f278ead442209dfc8f3895cd7735
출처 데이터셋
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09045433B2

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