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p-Toluenesulfonic acid → 2-(4-Methoxy-alpha-cumyl)-4-tert-butylphenol

HRID 392551
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HRID 392551 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([CH3:31])=[CH2:30])=[CH:27][CH:26]=1>C1(C)C=CC=CC=1>[CH3:23][O:24][C:25]1[CH:33]=[CH:32][C:28]([C:29]([C:9]2[CH:10]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[CH:6]=[CH:7][C:8]=2[OH:11])([CH3:31])[CH3:30])=[CH:27][CH:26]=1
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참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 73934-tert-ButylphenolHCID 2594141-Methoxy-4-(1-methylethenyl)benzene

생성물 1

HCID 226643652-(4-Methoxy-alpha-cumyl)-4-tert-butylphenol

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
65 °C

실험 절차

To a three-necked 500 mL flask equipped with a mechanical stirrer, 37 g of 4-tert-butylphenol, 100 mL of toluene and 2.4 g of p-toluenesulfonic acid are charged and heater to 55° C. The 4-methoxy-α-methylstyrene (40 g) prepared in Example 1 is added over 2.5 hours. The reaction mass is stirred for an additional three hours at 65° C. The reaction mass is then washed twice with 200 mL of saturated sodium bicarbonate solution and thrice with 100 mL of water. The solvent is removed by vacuum distillation and unreacted phenol and alkene are moved by Kugelrohr distillation at 100° C./0.16 mm Hg. The title compound is prepared in a yield of 78 g as a light brown oil whose structure is consistent with 1Hnmr and mass spectroscopy.

후처리

  1. customTo a three-necked 500 mL flask equipped with a mechanical stirrer
  2. customto 55° C
  3. washThe reaction mass is then washed twice with 200 mL of saturated sodium bicarbonate solution and thrice with 100 mL of water
  4. customThe solvent is removed by vacuum distillation and unreacted phenol and alkene
  5. distillationare moved by Kugelrohr distillation at 100° C./0.16 mm Hg

출처 및 근거

ORD 기록
ord-c09de909e67c44df9dc8c793cb8d4818
출처 데이터셋
uspto-grants-2004_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06800676B2

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