Acetone → 1-[2-[(2-Methyl-1-oxo-2-propen-1-yl)oxy]ethyl] 1,2-cyclohexanedicarboxylate

HRID 982588Notes

Reaction equation

HRID 982588 reaction equation
CC(C)=O.[C@@H:5]12[C:14](=[O:15])[O:13][C:11](=[O:12])[C@@H:6]1[CH2:7][CH2:8][CH2:9][CH2:10]2.[C:16]([O:21][CH2:22][CH2:23][OH:24])(=[O:20])[C:17]([CH3:19])=[CH2:18]>CN(C)C1C=CN=CC=1.O>[C:16]([O:21][CH2:22][CH2:23][O:24][C:11]([CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[C:14]([OH:13])=[O:15])=[O:12])(=[O:20])[C:17]([CH3:19])=[CH2:18]

Participants

6

Reactant 3

HCID 180AcetoneHCID 133602-Hydroxyethyl MethacrylateHCID 641660Hexahydrophthalic anhydride, cis-

Product 1

HCID 64523861-[2-[(2-Methyl-1-oxo-2-propen-1-yl)oxy]ethyl] 1,2-cyclohexanedicarboxylate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

To acetone (1,000 mL) were added cis-1,2-cyclohexanedicarboxylic anhydride (308.3 g), 2-hydroxyethyl methacrylate (273.3 g), and 4-dimethylaminopyridine (4.9 g). This mixture was heated with refluxing for 5 hours, and the acetone was distilled off under reduced pressure. Thereafter, 1N hydrochloric acid (500 mL) and ethyl acetate (2,000 mL) were added to the residue to extract it. The resulting organic phase was washed twice with saturated aqueous sodium chloride solution (500 mL), and anhydrous magnesium sulfate (100 g) was then added thereto. This mixture was allowed to stand for 1 hour to dehydrate the organic phase. Subsequently, the magnesium sulfate was removed by filtration and the ethyl acetate was distilled off under reduced pressure to obtain a white solid. The solid was pulverized and then added to water (2,000 mL). After this mixture was stirred for 2 hours, the particles were taken out by filtration and dried. As a result, 2-[2-(methacryloyloxy)ethoxy-carbonyl]cyclohexanecarboxylic acid was obtained as a white solid (518.9 g).

Workup

  1. temperatureThis mixture was heated
  2. temperaturewith refluxing for 5 hours
  3. distillationthe acetone was distilled off under reduced pressure
  4. additionThereafter, 1N hydrochloric acid (500 mL) and ethyl acetate (2,000 mL) were added to the residue
  5. extractionto extract it
  6. washThe resulting organic phase was washed twice with saturated aqueous sodium chloride solution (500 mL), and anhydrous magnesium sulfate (100 g)
  7. additionwas then added
  8. customSubsequently, the magnesium sulfate was removed by filtration
  9. distillationthe ethyl acetate was distilled off under reduced pressure
  10. customto obtain a white solid
  11. filtrationthe particles were taken out by filtration
  12. customdried

Sources & evidence

ORD record
ord-496862104c354afdab9ea352600e510b
Source dataset
uspto-grants-2005_03
Patent number
US06861200B2

Reaction notes

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