Methyl Acrylate → HCID 19782730, compound

HRID 1534679Notes

Reaction equation

HRID 1534679 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1O)([CH3:4])([CH3:3])[CH3:2].CC(C)([O-:19])C.[K+].CN1CCCC1=O.[C:29]([O:33][CH3:34])(=[O:32])[CH:30]=[CH2:31]>CO.O.C(O)(=O)C>[C:1]([C:5]1[CH:10]=[C:9]([OH:19])[CH:8]=[C:7]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:6]=1[CH2:31][CH2:30][C:29]([O:33][CH3:34])=[O:32])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 7294Methyl AcrylateHCID 13387N-methyl-2-pyrrolidoneHCID 314052,6-Di-tert-butylphenolHCID 23665647Potassium tert-butoxide

Product 1

HCID 19782730HCID 19782730, compoundYield 329.7%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
165 °C

Procedure

To a four neck round bottom flask, equipped with a mechanical stirrer, a three-way stopcock, a thermometer and a reflux condenser connected to a cold trap and an oil bubbler, were charged, under nitrogen atmosphere and at room temperature, 45.8 g (0.22 moles) 2,6-di-t-butylphenol and 7.48 g (0.067 moles) potassium t-butoxide. The reaction mixture was heated to 165° C. and t-butanol was removed from the reaction mixture by nitrogen purging and collected in the cold trap. After approximately 10 minutes substantially all of the t-butanol had been removed, 6.4 ml (0.067 moles) N-methylpyrrolidinone were added and stirring continued. Next the reaction mixture, while stirring, was cooled down to 120° C. over a 5 minute period. Then 21 ml (0.23 moles) methyl acrylate were added all at once. The temperature dropped to 105° C. then rose to 139° C. in approximately 2 minutes. When the reaction was completed, the reaction mixture was cooled to about 90° C. and acidified with 4 ml of glacial acetic acid. Then the acidified mixture was diluted with a solution of 40 ml methanol and 8 ml water, allowed to cool to room temperature and the product was filtered. 64.6 g of methyl 3-(2,6-di-t-butyl-4-hydroxyphenyl)propionate was obtained.

Workup

  1. customTo a four neck round bottom flask, equipped with a mechanical stirrer
  2. customa three-way stopcock, a thermometer and a reflux condenser connected to a cold trap
  3. additionan oil bubbler, were charged, under nitrogen atmosphere and at room temperature
  4. customt-butanol was removed from the reaction mixture by nitrogen purging
  5. customcollected in the cold trap
  6. customAfter approximately 10 minutes substantially all of the t-butanol had been removed
  7. stirringNext the reaction mixture, while stirring
  8. temperaturewas cooled down to 120° C. over a 5 minute period
  9. additionThe temperature dropped to 105° C.
  10. temperaturethe reaction mixture was cooled to about 90° C.
  11. temperatureto cool to room temperature
  12. filtrationthe product was filtered

Sources & evidence

ORD record
ord-cbc86bb8a6ed4baba2866e8fd4b09876
Source dataset
uspto-grants-1992_02
Patent number
US05089656

Reaction notes

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