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

HRID 437104Notes

Reaction equation

HRID 437104 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideCatalyst

Procedure

A one-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° C. to 155° C. at .15 milliliters of mercury pressure.

Workup

  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

Sources & evidence

ORD record
ord-f1bc98d48b9c4069b28d86475f96978e
Source dataset
uspto-grants-1977_06
Patent number
US04029713

Reaction notes

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