2-Chlorobenzaldehyde → HCID 54282972, compound

HRID 1003737Notes

Reaction equation

HRID 1003737 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[CH2:5][C:6]([CH2:8][O:9][CH2:10][CH2:11][I:12])=[O:7])[CH3:2].[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=O.N1CCCCC1>C(O)(C)C.C(O)(=O)C.N1CCCCC1>[CH2:1]([O:3][C:4](=[O:13])[C:5](=[CH:17][C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[Cl:14])[C:6]([CH2:8][O:9][CH2:10][CH2:11][I:12])=[O:7])[CH3:2]

Participants

6

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 8082PiperidineHCID 15428864HCID 15428864, compound

Product 1

HCID 54282972HCID 54282972, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 9793820Piperidine, acetateCatalystHCID 3776IsopropanolSolvent

Procedure

10 g (33 millimoles) of ethyl-4-(2-iodoethoxy)-acetoacetate (XIII) and 4.64 g (33 millimoles) of 2-chloro-benzaldehyde (V) are reacted in 100 ml of isopropanol in the presence of a piperidine acetate catalyst [0.28 g (3.3 millimoles) of piperidine+0.198 g (3.3 millimoles) of acetic acid] at room temperature for 10 hours. The reaction mixture is evaporated, the residual oil dissolved in dichloro methane, washed with water and dried. The organic phase is evaporated in vacuo. Thus 11.55 g of the desired product are obtained in the form of a reddish brown oil, yield 83%.

Workup

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

Sources & evidence

ORD record
ord-b7f453c806044400ada821e59cc902a5
Source dataset
uspto-grants-2000_04
Patent number
US06046337

Reaction notes

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