Hydroquinone → 4-(3,5-Di-t-butyl-4-hydroxyphenyl)-2-butyl methacrylate

HRID 1729766노트

반응식

HRID 1729766 반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH2:16][CH2:17][CH:18]([OH:20])[CH3:19])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].C1(C=CC(O)=CC=1)O.[C:29](OC)(=[O:33])[C:30]([CH3:32])=[CH2:31]>CC([O-])C.CC([O-])C.CC([O-])C.CC([O-])C.[Ti+4]>[C:29]([O:20][CH:18]([CH2:17][CH2:16][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[C:10]([OH:11])=[C:9]([C:12]([CH3:13])([CH3:15])[CH3:14])[CH:8]=1)[CH3:19])(=[O:33])[C:30]([CH3:32])=[CH2:31]

참가 물질

5

반응물 3

HCID 785HydroquinoneHCID 6658Methyl MethacrylateHCID 212743504-(3,5-Di-t-butyl-4-hydroxyphenyl) butane-2-ol

생성물 1

HCID 213178754-(3,5-Di-t-butyl-4-hydroxyphenyl)-2-butyl methacrylate수율 95%

시약·촉매·용매 1

HCID 11026Titanium isopropoxide촉매

실험 절차

A 1 liter flask was charged with a mixture of 69.5 grams (0.25 mole) of 4-(3,5-di-t-butyl-4-hydroxyphenyl) butane-2-ol, 350 milliliters of methyl methacrylate, 0.5 gram of hydroquinone and 5 grams of tetraisopropyl titanate as the catalyst. The mixture was heated to reflux and a methanolmethylmethacrylate azeotrope slowly distilled off over a 3.5 hour period. The reaction flask was cooled slightly and 25 milliliters of water was added dropwise to hydrolyze the catalyst. The reaction mixture was allowed to cool to room temperature. The mixture was stirred 15 minutes longer and then filtered through diatomaceous earth. One hundred milliliters of hexane was added to the filtrate which separated into organic and inorganic phases. The organic phase containing the product in hexane was separated and dried over magnesium sulfate. The hexane was evaporated to obtain 82 grams (95 percent) of 4-(3,5-di-t-butyl-4-hydroxyphenyl)-2-butyl methacrylate. The boiling point of this compound was 150° to 155° C at 0.15 milliliters of mercury pressure.

후처리

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. distillationa methanolmethylmethacrylate azeotrope slowly distilled off over a 3.5 hour period
  4. temperatureThe reaction flask was cooled slightly
  5. addition25 milliliters of water was added dropwise
  6. filtrationfiltered through diatomaceous earth
  7. additionOne hundred milliliters of hexane was added to the filtrate which
  8. customseparated into organic and inorganic phases
  9. additionThe organic phase containing the product in hexane
  10. customwas separated
  11. dry with materialdried over magnesium sulfate
  12. customThe hexane was evaporated

출처 및 근거

ORD 기록
ord-b54009503e6441b192ec0ae627c924cd
출처 데이터셋
uspto-grants-1976_11
특허 번호
US03989741

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