2,3-Dichlorobenzaldehyde → Cyclopentyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate

HRID 1789015Notes

Reaction equation

HRID 1789015 reaction equation
[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[O:11]=[C:12]([CH3:22])[CH2:13][C:14]([O:16][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:15]>N1CCCCC1.C(O)(=O)CCCCC.C1C=CC=CC=1>[Cl:1][C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[C:13]([C:12](=[O:11])[CH3:22])[C:14]([O:16][CH:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)=[O:15]

Participants

6

Reactant 2

HCID 357452,3-DichlorobenzaldehydeHCID 243706Cyclopentyl 3-oxobutanoate

Product 1

HCID 54059666Cyclopentyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoateYield 109%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 8892Hexanoic AcidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 2,3-dichlorobenzaldehyde (2.5 g, 14.3 mmoles), cyclopentyl 3-oxobutanoate (2.42 g, 14.3 mmoles), piperidine (8 drops) and hexanoic acid (11 drops) in dry benzene (80 ml) was heated at reflux for 4 hours using a Dean and Stark apparatus. The solution was allowed to cool to room temperature and the solvent removed in vacuo to leave the sub-title compound as an oil 5.1 g.

Workup

  1. temperatureat reflux for 4 hours
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-8868992fd39742ee9646853c3df9c183
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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