Hydrochloric Acid → 5,7-di-tert-butyl-3-(4-methylthiophenyl)-3H-benzofuran-2-one

HRID 440149

반응식

HRID 440149 반응식
[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[CH:10](O)[C:9]=2[CH:15]=1)([CH3:4])([CH3:3])[CH3:2].[C:20]1([S:26][CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl>C(Cl)Cl.O>[C:1]([C:5]1[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]2[O:12][C:11](=[O:13])[CH:10]([C:23]3[CH:24]=[CH:25][C:20]([S:26][CH3:27])=[CH:21][CH:22]=3)[C:9]=2[CH:15]=1)([CH3:3])([CH3:4])[CH3:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 7520Thioanisole2회HCID 6451240Aluminum(III) ChlorideHCID 68508215,7-Di-tert-butyl-3-hydroxy-2-benzofuranone2회

생성물 1

HCID 215775455,7-di-tert-butyl-3-(4-methylthiophenyl)-3H-benzofuran-2-one수율 18.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

반응 조건

온도
80 °C

실험 절차

A solution of 26.2 g (0.10 mol) of 5,7-di-tert-butyl-3-hydroxy-3H-benzofuran-2-one (compound (201), Table 2, Example 1a) in 25 ml (0.21 mol) of thioanisole is added dropwise to a solution of 14.7 g (0.11 mol) of aluminium chloride in 15 ml (0.13 mol) of thioanisole at 35°-40° C. The reaction mixture is thereafter stirred for 30 minutes at 30° C. and for 2 hours at 80° C., and then after cooling, c. 50 ml of water and then concentrated hydrochloric acid and methylene chloride are added cautiously in sufficient amount to form a homogeneous two-phase mixture. The organic phase is separated, washed with water, dried over sodium sulfate and concentrated on a vacuum rotary evaporator. Crystallisation of the residue from ethanol yields 6.7 g (18% ) of 5,7-di-tert-butyl-3-(4-methylthiophenyl)-3H-benzofuran-2-one, m.p. 125°-131° C. (compound (108), Table 1).

후처리

  1. temperatureafter cooling
  2. customto form a homogeneous two-phase mixture
  3. customThe organic phase is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated on a vacuum rotary evaporator
  7. customCrystallisation of the residue from ethanol

출처 및 근거

ORD 기록
ord-886248421c8b4875a19e9a138b25eee2
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516920

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