Methyl Acrylate → Methyl di-t-butyl hydroxyhydrocinnamate

HRID 570065Notes

Reaction equation

HRID 570065 reaction equation
[K].[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:7]=1[OH:16])([CH3:5])([CH3:4])[CH3:3].[C:17]([O:21][CH3:22])(=[O:20])[CH:18]=[CH2:19]>C(O)(C)(C)C>[C:12]([C:8]1[CH:9]=[C:10]([CH2:19][CH2:18][C:17]([O:21][CH3:22])=[O:20])[CH:11]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[C:7]=1[OH:16])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 314052,6-Di-tert-butylphenolHCID 5462222Potassium

Product 1

HCID 62603Methyl di-t-butyl hydroxyhydrocinnamate

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
50 °C

Procedure

To 500 parts by volume of dry t-butyl alcohol in a flask fitted with mechanical stirrer, inert gas inlet, thermometer, condenser and dropping funnel are added 2.1 parts of potassium metal. After the ensuing reaction is complete, there are added 37.3 parts of 2,6-di-t-butylphenol, followed rapidly by 17.7 parts of methyl acrylate. The stirred reaction mixture is heated to 50° C. for 18 hours and allowed to cool. The solvent is removed under reduced pressure and the residual mass neutralized by addition of dilute hydrochloric acid. This mixture is then extracted with two portions of 200 parts by volume each of ethyl ether. The combined ethereal extracts are washed with two portions of 100 parts by volume each of water and then dried over anhydrous sodium sulfate. The ether layer is removed by filtration and concentrated on a steam bath. The residual oily mass is then vacuum distilled. The fraction collected at 125°-130 °C./0.1 mm Hg crystallizes upon standing to yield methyl 3-(3,5-di-t-butyl-4-hydroxyphenyl)propionate, M.P. 63.0°-64.5° C. Rerystallization from hexane yields a white solid, M.P. 66°-66.5° C.

Workup

  1. customthermometer, condenser and dropping
  2. customAfter the ensuing reaction
  3. customThe stirred reaction mixture
  4. temperatureto cool
  5. customThe solvent is removed under reduced pressure
  6. additionthe residual mass neutralized by addition of dilute hydrochloric acid
  7. extractionThis mixture is then extracted with two portions of 200 parts by volume each of ethyl ether
  8. washThe combined ethereal extracts are washed with two portions of 100 parts by volume each of water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customThe ether layer is removed by filtration
  11. concentrationconcentrated on a steam bath
  12. distillationvacuum distilled
  13. customThe fraction collected at 125°-130 °C./0.1 mm Hg
  14. customcrystallizes

Sources & evidence

ORD record
ord-70bdcd3336e1465da1fe5b529843e355
Source dataset
uspto-grants-1988_03
Patent number
US04734519

Reaction notes

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