Benzene → HCID 13280229, 화합물

HRID 1918417노트

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HRID 1918417 반응식
[CH:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl-].[Cl-].[Al+3].[C:11](Cl)(=[O:16])/[C:12](=[CH:14]/[CH3:15])/[CH3:13]>Cl>[CH3:13][CH:12]1[CH:14]([CH3:15])[C:6]2[C:1](=[CH:2][CH:3]=[CH:4][CH:5]=2)[C:11]1=[O:16]

참가 물질

5

반응물 3

HCID 241BenzeneHCID 5325503(2E)-2-Methyl-2-butenoyl chlorideHCID 6451240Aluminum(III) Chloride

생성물 1

HCID 13280229HCID 13280229, 화합물수율 92%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

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온도
7 °C

실험 절차

Under an argon atmosphere benzene (335 ml, 3.74 mol) and aluminum trichloride (90.78 g, 0.68 mol) were introduced into a 1 liter three necked round bottomed flask fitted with a magnetic stirring apparatus, an addition funnel and a reflux condenser. The stirred orange mixture was cooled to 7° C. and tigloyl chloride (33) (40 g, 0.34 mol) was added dropwise via an addition funnel. After completion of the addition, the mixture was allowed to come to room temperature and then refluxed overnight. Then the reaction mixture was allowed to come to room temperature and poured onto mixture of ice (300 g) and conc. HCl (50 ml). The organic layer was separated and washed with a saturated solution of sodium bicarbonate (3×100 ml), then dried over magnesium sulfate and filtered. The excess benzene was removed under reduced pressure to afford (34) (50.02 g, 92%) as a yellow liquid. The 1H NMR spectrum was identical with the literature (T. E. Ready, J. C. W. Chien, M. D. Rausch, J. Org. Chem. 1999 583, 11-27; J. Sarrazin, A. Tallec, Tetrahedron Letters, 1977, 18, 1579-1582; M. Hiscock, G. B. Porter, J. Chem. Soc. (B), 1971, 1631-1634). 1H NMR (200 MHz, CDCl3): δ [ppm] 7.76-7.34 (m, 4H, arom), 2.94 (dq, 3J=4.9 Hz, 3J=7.0 Hz, 1H, H-position 2), 2.24 (dq, 3J=7.3 Hz, 3J=4.7 Hz, 1H, H-position 3), 1.46 (d, 3J=6.9 Hz, 3H, CH3-position 2), 1.32 (d, 3J=7.3 Hz, 3H, CH3-position 3).

후처리

  1. customfitted with a magnetic stirring apparatus, an addition funnel and a reflux condenser
  2. additionAfter completion of the addition
  3. customto come to room temperature
  4. temperaturerefluxed overnight
  5. customto come to room temperature
  6. customThe organic layer was separated
  7. washwashed with a saturated solution of sodium bicarbonate (3×100 ml)
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customThe excess benzene was removed under reduced pressure

출처 및 근거

ORD 기록
ord-0b14174ad6e1446fbdc0a1b6c269f029
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618328B2

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