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

HRID 1793278Notes

Reaction equation

HRID 1793278 reaction equation
C[C:2]([CH3:4])=[O:3].[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]([OH:21])(=[O:20])[C:17]([CH3:19])=[CH2:18]>O>[C:16]([O:21][CH2:4][CH2:2][O:3][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

5

Reactant 3

HCID 180AcetoneHCID 4093Methacrylic AcidHCID 641660Hexahydrophthalic anhydride, cis-

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into acetone (1,000 ml) were dissolved cis-1,2-cyclohexane dicarboxylic anhydride (308.3 g), methacrylic acid (2-hydroxyethyl) (273.3 g) and 4-(dimethylamine) pyridine (4.9 g), and heated for 5 hours under reflux. After acetone had been distilled off under reduced pressure, 1N hydrochloric acid (500 ml) and ethyl acetate (2,000 ml) were added thereto so that an extracting process was carried out. After the organic layer had been washed with saturated saline solution (500 ml) twice, to this was added magnesium sulfuric anhydride (100 g) and this was allowed to stand for 1 hour to be dehydrated. After magnesium sulfate had been filtered and separated, ethyl acetate was distilled off under reduced pressure so that a white solid matter was obtained. After having been ground, this was added to water (2,000 ml), and after having been stirred for 2 hours, this was filtered and dried to obtain a white solid matter (518.9 g) of 2-[2-(methacryloyloxy)ethoxycarbonyl]cyclohexane carboxylic acid.

Workup

  1. temperatureheated for 5 hours
  2. temperatureunder reflux
  3. distillationAfter acetone had been distilled off under reduced pressure, 1N hydrochloric acid (500 ml) and ethyl acetate (2,000 ml)
  4. additionwere added
  5. washAfter the organic layer had been washed with saturated saline solution (500 ml) twice
  6. additionto this was added magnesium sulfuric anhydride (100 g)
  7. filtrationAfter magnesium sulfate had been filtered
  8. customseparated
  9. distillationethyl acetate was distilled off under reduced pressure so that a white solid matter
  10. customwas obtained
  11. filtrationthis was filtered
  12. customdried

Sources & evidence

ORD record
ord-156955290ae845ef8c4c29c66f5866ca
Source dataset
uspto-grants-2006_07
Patent number
US07081329B2

Reaction notes

Loading…