Cyclopropanecarboxaldehyde → HCID 11457694, compound

HRID 618858Notes

Reaction equation

HRID 618858 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([O-])=O.[CH:9]1([CH:12]=O)C[CH2:10]1.C([O-])(=O)C.[NH4+]>C1C=CC=CC=1.N1C=CC=CC=1>[CH:9]1([C:2](=[CH2:3])[C:1]([O:7][CH3:8])=[O:6])[CH2:12][CH2:10]1

Participants

6

Reactant 3

HCID 123114Cyclopropanecarboxaldehyde2×HCID 517165Ammonium AcetateHCID 3801157Monomethyl malonate

Product 1

HCID 11457694HCID 11457694, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 1049PyridineSolvent

Procedure

To a solution of monomethyl malonate (14.16 g, 1.2 eq based on the cyclopropanecarboxaldehyde) and ammonium acetate (0.3 g) in benzene (20 ml) was added dropwise a solution of cyclopropanecarboxaldehyde (7.1 g, 101.3 mmol) in pyridine (11 ml) at 0±5° C. After addition, the solution was refluxed to remove water outside. To the reaction mixture was added 1N hydrochloric acid to acidify. After separation, the aqueous layer was extracted with diisopropyl ether (70 ml) twice. The combined organic layer was concentrated under reduced pressure to give methyl cyclopropylacrylate (11.1 g, yield 88%).

Workup

  1. additionAfter addition
  2. temperaturethe solution was refluxed
  3. customto remove water outside
  4. additionTo the reaction mixture was added 1N hydrochloric acid
  5. customAfter separation
  6. extractionthe aqueous layer was extracted with diisopropyl ether (70 ml) twice
  7. concentrationThe combined organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-47311248db07488c81fbddb0b8c772f3
Source dataset
uspto-grants-1999_09
Patent number
US05955627

Reaction notes

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