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Sulfuric Acid → 4-(4-tert-Butylphenyl)-2-(propan-2-yl)-1H-indene

HRID 1392352
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HRID 1392352 반응식
[BH4-].[Na+].[CH:3]([CH:6]1[CH2:14][C:13]2[C:8](=[C:9]([C:15]3[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=3)[CH:10]=[CH:11][CH:12]=2)[C:7]1=O)([CH3:5])[CH3:4].C1(C)C=CC=CC=1.S(=O)(=O)(O)O>CO>[CH:3]([C:6]1[CH2:14][C:13]2[C:8]([CH:7]=1)=[C:9]([C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH3:23])([CH3:22])[CH3:24])=[CH:17][CH:16]=1)[CH:10]=[CH:11][CH:12]=2)([CH3:5])[CH3:4]
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참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 1140TolueneHCID 4311764Sodium borohydrideHCID 231055462-Isopropyl-7-(4'-tert-butylphenyl)-1-indanone

생성물 1

HCID 179804054-(4-tert-Butylphenyl)-2-(propan-2-yl)-1H-indene수율 96.3%

시약·촉매·용매 1

HCID 887Methanol
용매

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온도
50 °C

실험 절차

4.83 g of sodium borohydride and 39.1 g of 2-isopropyl-7-(4′-tert-butylphenyl)-1-indanone together with 118 ml of toluene are placed in a reaction vessel. At 50° C., 22.5 ml of methanol are slowly added and the reaction mixture is stirred for 6 hours at 50° C. After cooling to room temperature, 50 ml of 2N sulfuric acid are added and the mixture is stirred vigorously for another 30 minutes. The mixture is subsequently transferred to a separating funnel, the phases are separated and the aqueous phase is shaken twice with a total of 60 ml of 2N sulfuric acid. The organic phases are combined and dried over magnesium sulfate. The solvent of the reaction mixture is removed virtually completely and 200 ml of toluene and 0.4 g of p-toluenesulfonic acid are subsequently added to the residue. Water is distilled from the reaction mixture by heating for 1.5 hours on a water separator until reaction is complete. The reaction mixture is subsequently washed once with 100 ml of saturated sodium hydrogen carbonate solution and dried over magnesium sulfate. After separating off the magnesium sulfate, the residue is dried in an oil pump vacuum. This gives 35.7 g of 2-isopropyl-4-(4′-tert-butylphenyl)indene (total yield: 96%).

후처리

  1. temperatureAfter cooling to room temperature
  2. stirringthe mixture is stirred vigorously for another 30 minutes
  3. customThe mixture is subsequently transferred to a separating funnel
  4. customthe phases are separated
  5. stirringthe aqueous phase is shaken twice with a total of 60 ml of 2N sulfuric acid
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent of the reaction mixture is removed virtually completely
  8. addition200 ml of toluene and 0.4 g of p-toluenesulfonic acid are subsequently added to the residue
  9. distillationWater is distilled from the reaction mixture
  10. temperatureby heating for 1.5 hours on a water separator until reaction
  11. washThe reaction mixture is subsequently washed once with 100 ml of saturated sodium hydrogen carbonate solution
  12. dry with materialdried over magnesium sulfate
  13. customAfter separating off the magnesium sulfate
  14. customthe residue is dried in an oil pump vacuum

출처 및 근거

ORD 기록
ord-e5a39ebceb5c41328afe5f714c5d5dc4
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07342078B2

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