1,3-Butadiene → Spiro[5.5]undeca-1,4,8-trien-3-one, 2,4-bis(1,1-dimethylethyl)-

HRID 638663

반응식

HRID 638663 반응식
CN([CH2:4][C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)C.[CH2:20]=[CH:21][CH:22]=[CH2:23]>C1(C)C=CC=CC=1>[C:16]([C:7]1[C:8](=[O:15])[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:10][C:5]2([CH2:23][CH2:22][CH:21]=[CH:20][CH2:4]2)[CH:6]=1)([CH3:19])([CH3:18])[CH3:17]

참가 물질

4

반응물 2

HCID 78451,3-ButadieneHCID 66609Phenol, 4-[(dimethylamino)methyl]-2,6-bis(1,1-dimethylethyl)-

생성물 1

HCID 10730920Spiro[5.5]undeca-1,4,8-trien-3-one, 2,4-bis(1,1-dimethylethyl)-수율 94%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
205 °C

실험 절차

A 300 mL Parr autoclave was charged with a solution of 10.52 g (40 mmols) of N,N-dimethyl-4-aminomethyl-2,6-di-t-butylphenol in 90 g of toluene, sealed and evacuated by a water aspirator, and then charged with 4.38 g (80 mmols) of 1,3-butadiene. The reaction mixture was heated to approximately 205° C. for 10 hours. A maximum pressure of 120 psig was obtained. After cooling, the reaction mixture was poured into a 500 mL separatory funnel, washed with approximately 2N HCl (1×50 mLs), water (1×50 mLs), and brine (1×50 mLs), dried over anhydrous magnesium sulfate, and concentrated in vacuo to afford 10.21 g (94% yield) of 2,4-di-t-butylspiro[5.5]undeca-1,4,8-trien-3-one as a brown solid. The brown solid was recrystallized from 80% ethanol to give the product as colorless crystals.

후처리

  1. customsealed
  2. customevacuated by a water aspirator
  3. customA maximum pressure of 120 psig was obtained
  4. temperatureAfter cooling
  5. additionthe reaction mixture was poured into a 500 mL separatory funnel
  6. washwashed with approximately 2N HCl (1×50 mLs), water (1×50 mLs), and brine (1×50 mLs)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-308ab92597114a43936482aa9f6f2583
출처 데이터셋
uspto-grants-1985_12
특허 번호
US04562294

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