Acetic Acid → Propanedioic acid, [(2-chlorophenyl)methylene]-, diethyl ester

HRID 621421Notes

Reaction equation

HRID 621421 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[C:10]([O:18][CH2:19][CH3:20])(=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13].C(O)(=O)C.N1CCCCC1>C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]([O:18][CH2:19][CH3:20])=[O:17]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 69962-ChlorobenzaldehydeHCID 7761Diethyl MalonateHCID 8082Piperidine

Product 1

HCID 297307Propanedioic acid, [(2-chlorophenyl)methylene]-, diethyl ester

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A mixture of 97% chlorobenzaldehyde (51.5 g, 41.3 ml, 0.35 mole), diethyl malonate (57 g, 54 ml, 0.35 mole), acetic acid (1 ml) and piperdine (2 ml) in benzene (150 ml) was heated under reflux with azeotropic removal of water overnight. Benzene was removed by distillation, the residue was diluted with ethyl acetate (200 ml), washed with 10% hydrochloric acid, saturated potassium bicarbonate, brine and dried over anhydrous magnesium sulfate and concentrated in vacuo to yield 100 g of the title A compound as an oil.

Workup

  1. temperaturewas heated
  2. customBenzene was removed by distillation
  3. additionthe residue was diluted with ethyl acetate (200 ml)
  4. washwashed with 10% hydrochloric acid, saturated potassium bicarbonate, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40bbc4e562964204a5c0d8fda5f8920e
Source dataset
uspto-grants-1989_04
Patent number
US04824831

Reaction notes

Loading…