2-Chlorobenzaldehyde → HCID 54543583, compound

HRID 1003736Notes

Reaction equation

HRID 1003736 reaction equation
[Cl:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[CH2:10]([O:12][C:13](=[O:22])[CH2:14][C:15]([CH2:17][O:18][CH2:19][CH2:20][Cl:21])=[O:16])[CH3:11].N1CCCCC1>C(O)(C)C.C(O)(=O)C.N1CCCCC1>[CH2:10]([O:12][C:13](=[O:22])[C:14](=[CH:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[Cl:1])[C:15]([CH2:17][O:18][CH2:19][CH2:20][Cl:21])=[O:16])[CH3:11]

Participants

6

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 8082PiperidineHCID 15428861HCID 15428861, compound

Product 1

HCID 54543583HCID 54543583, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 9793820Piperidine, acetateCatalystHCID 3776IsopropanolSolvent

Procedure

16.64 g (0.118 mole) of 2-chloro-benzaldehyde (V) and 24.7 g (0.118 mole) of ethyl-4-(2-chloroethoxy)-acetoacetate (IV) are reacted in 365 ml of isopropanol in the presence of a piperidine acetate catalyst [10 g (11.8 millimoles) of piperidine+0.7 g (11.8 millimoles) of acetic acid] at room temperature for 10 hours. The reaction mixture is evaporated, the residual oil is dissolved in dichloro methane, washed with water and dried. The organic phase is evaporated in vacuo. Thus 37.9 g of the desired product are obtained in the form of a yellow oil, yield 97%.

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residual oil is dissolved in dichloro methane
  3. washwashed with water
  4. customdried
  5. customThe organic phase is evaporated in vacuo

Sources & evidence

ORD record
ord-8f53d5c582bb4f5aab61dedae0a15b06
Source dataset
uspto-grants-2000_04
Patent number
US06046337

Reaction notes

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