Acetic Acid → HCID 53697886, compound

HRID 249593

Reaction equation

HRID 249593 reaction equation
[CH3:1][O:2][C:3](=[O:9])[CH2:4][C:5]([CH2:7][Cl:8])=[O:6].[CH:10](=O)[CH2:11][CH3:12].C(O)(=O)C>ClCCl.N1CCCCC1>[CH3:1][O:2][C:3](=[O:9])[C:4](=[CH:10][CH2:11][CH3:12])[C:5]([CH2:7][Cl:8])=[O:6]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 527PropanalHCID 36240Methyl 4-chloroacetoacetate

Product 1

HCID 53697886HCID 53697886, compoundYield 92.3%

Reagents, catalysts & solvents 2

HCID 8082PiperidineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-27 °C

Procedure

To a solution of 4-chloroacetoacetic acid methyl ester (700 mg : 4.65 mMol.) and propionaldehyde (405 mg : 6.97 mMol.) and acetic acid (28 mg : 0.47 mMol.) in dichloromethane (3 ml) is added a solution of piperidine (24 mg : 0.28 mMol.) in dichloromethane (0.5 ml), and the mixture is stirred at -27° C. for 120 minutes. The reaction mixture is washed with dilute hydrochloric acid and water and concentrated under reduced pressure at lower than 15° C. to give 4-chloro-2-propylideneacetoacetic acid methyl ester (818 mg). Yield: 92%.

Workup

  1. washThe reaction mixture is washed with dilute hydrochloric acid and water
  2. concentrationconcentrated under reduced pressure at lower than 15° C.

Sources & evidence

ORD record
ord-5413e0af0a7f4eb0b52b772f16d2a1b8
Source dataset
uspto-grants-1993_05
Patent number
US05214037

Linked notes

Loading…