Methyl Acrylate → Methyl di-t-butyl hydroxyhydrocinnamate

HRID 1446370Notes

Reaction equation

HRID 1446370 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH:2]=[CH2:3].[C:7]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[C:12]=1[OH:21])([CH3:10])([CH3:9])[CH3:8]>>[C:17]([C:13]1[CH:14]=[C:15]([CH:16]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:12]=1[OH:21])[CH2:3][CH2:2][C:1]([O:5][CH3:6])=[O:4])([CH3:20])([CH3:19])[CH3:18]

Participants

3

Reactant 2

HCID 7294Methyl AcrylateHCID 314052,6-Di-tert-butylphenol

Product 1

HCID 62603Methyl di-t-butyl hydroxyhydrocinnamate

Conditions

Temperature
140 °C

Procedure

The reaction was heated to 140° C. to remove the water/toluene azeotrope. A white slurry was obtained and 7.2 g hazy toluene was collected in the trap. The Dean-Stark trap was removed and a cooling condenser was connected to the reactor. The heating was reset to 120° C. Vigorous condensation was observed and 99.1 g (1.15 mol) of methyl acrylate was added over a 45-minute period. After three hours of heating at 120° C., the 2,6-di-tert-butylphenol conversion was about 98.5% complete.

Workup

  1. customto remove the water/toluene azeotrope
  2. customA white slurry was obtained
  3. custom7.2 g hazy toluene was collected in the trap
  4. customThe Dean-Stark trap was removed
  5. customa cooling condenser was connected to the reactor
  6. customwas reset to 120° C
  7. customVigorous condensation
  8. temperatureAfter three hours of heating at 120° C.

Sources & evidence

ORD record
ord-13e8ad6454864e4182cc489d468760b4
Source dataset
uspto-grants-2010_02
Patent number
US07667066B2

Reaction notes

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