Hydrochloric Acid → 1-Methyl-3-(4-t-butylphenyl)-cyclopentadiene

HRID 602847

반응식

HRID 602847 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:17][CH:18]1[CH2:22][CH2:21][CH2:20][C:19]1=O.Cl>C(OCC)C.CCCCCC>[CH3:17][C:18]1[CH2:22][CH:21]=[C:20]([C:2]2[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][CH:3]=2)[CH:19]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 142652-MethylcyclopentanoneHCID 775951-Bromo-4-tert-butylbenzeneHCID 178418339Butyllithium

생성물 1

HCID 866295701-Methyl-3-(4-t-butylphenyl)-cyclopentadiene수율 69.3%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

실험 절차

1-Bromo-4-t-butylbenzene (18 mL, 104 mmol) was dissolved in diethyl ether (100 mL) and added dropwise at −30° C. with a solution (66 mL, 104 mmol, 1.57 N) of n-butyllithium in hexane. The resultant solution was warmed to room temperature, stirred night and day and added dropwise at −20° C. to a solution of 3-methyl-2-cyclopentanone (10 g, 104 mmol) in diethyl ether (10 mL). Immediately after dropwise addition, the solution was warmed to room temperature and stirred for 3 hours. After termination of the reaction, the reaction solution was added with dilute hydrochloric acid and subjected to layer separation. The organic layer was dried with magnesium sulfate and then had the solvent distilled off under reduced pressure. The crude product was distilled under reduced pressure (105 to 115° C./0.16 mmHg) to obtain 1-methyl-3-(4-t-butylphenyl)-cyclopentadiene (15.3 g, yield: 69%).

후처리

  1. additionImmediately after dropwise addition
  2. stirringstirred for 3 hours
  3. customAfter termination of the reaction
  4. customsubjected to layer separation
  5. dry with materialThe organic layer was dried with magnesium sulfate
  6. distillationdistilled off under reduced pressure
  7. distillationThe crude product was distilled under reduced pressure (105 to 115° C./0.16 mmHg)

출처 및 근거

ORD 기록
ord-1f47fe57eb444ffb856be1ac35fc2d0f
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906599B2

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