Acetoin → HCID 19357483, compound

HRID 526805

Reaction equation

HRID 526805 reaction equation
[OH:1][CH:2]([CH3:6])[C:3](=[O:5])[CH3:4].C(N(CC)CC)C.[C:14](Cl)(=[O:18])[C:15]([CH3:17])=[CH2:16]>C(Cl)Cl.COC1C=CC(O)=CC=1>[C:14]([O:5][CH:3]([C:2](=[O:1])[CH3:6])[CH3:4])(=[O:18])[C:15]([CH3:17])=[CH2:16]

Participants

6

Reactant 3

HCID 179AcetoinHCID 8471TriethylamineHCID 13528Methacryloyl chloride

Product 1

HCID 19357483HCID 19357483, compoundYield 53.1%

Reagents, catalysts & solvents 2

HCID 90154-MethoxyphenolCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
5 °C

Procedure

In a 2 L four-necked flask subjected replacement with nitrogen, 150 g of 3-hydroxy-2-butanone (made by Tokyo Chemical Industry Co., Ltd., purity: 95.0% or more) was put, and dissolved in 750 g of methylene chloride, and a stirrer, a thermometer and a Dimroth cooling tube were connected thereto. After the solution was stirred and cooled to about 5° C., 190 g of triethylamine and 80 mg of p-methoxyphenol were added thereto. While the solution was cooled to about 5° C. under stirring, 178 g of methacryloyl chloride was slowly added dropwise thereto over 4 hours, and further stirred for 30 minutes after completion of the dropwise addition to allow a reaction. The resulting reaction mixture was washed with 1 N-hydrochloric acid, a 10% sodium carbonate aqueous solution and saturated brine at room temperature, dried over anhydrous magnesium sulfate and separated by filtration to obtain a reaction crude liquid. The solvent of the reaction crude liquid was distilled off using an evaporator, 80 mg of p-methoxyphenol was added thereto and the resulting solution was distilled under reduced pressure to give 141 g of 3-oxobutane-2-yl methacrylate of 96.5% GC purity (yield: 53.1% based on 3-hydroxy-2-butanone).

Workup

  1. customIn a 2 L four-necked flask subjected
  2. temperaturea stirrer, a thermometer and a Dimroth cooling tube
  3. temperatureWhile the solution was cooled to about 5° C.
  4. stirringunder stirring
  5. stirringfurther stirred for 30 minutes
  6. additionafter completion of the dropwise addition
  7. customa reaction
  8. customThe resulting reaction mixture
  9. washwas washed with 1 N-hydrochloric acid
  10. dry with materiala 10% sodium carbonate aqueous solution and saturated brine at room temperature, dried over anhydrous magnesium sulfate
  11. customseparated by filtration
  12. customto obtain
  13. customa reaction crude liquid
  14. customThe solvent of the reaction crude liquid
  15. distillationwas distilled off
  16. customan evaporator, 80 mg of p-methoxyphenol
  17. additionwas added
  18. distillationthe resulting solution was distilled under reduced pressure

Sources & evidence

ORD record
ord-33fe739cceb54b13a9279ebb70c7a281
Source dataset
uspto-grants-2016_05
Patent number
US09346775B2

Linked notes

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