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

HRID 1789019Notes

Reaction equation

HRID 1789019 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]([CH3:21])[CH2:13][C:14]([O:16][CH:17]1[CH2:20][O: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])[CH3:21])[C:14]([O:16][CH:17]1[CH2:20][O:19][CH2:18]1)=[O:15]

Participants

6

Reactant 2

HCID 357452,3-DichlorobenzaldehydeHCID 201893293-Oxetanyl 3-oxobutanoate

Product 1

HCID 57031759(3-Oxetanyl) 2-(2,3-dichlorophenylmethylene)-3-oxobutanoateYield 121.1%

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 8892Hexanoic AcidCatalystHCID 241BenzeneSolvent

Procedure

A solution of 2,3-dichlorobenzaldehyde (1.33 g, 7.6 mmoles), 3-oxetanyl 3-oxobutanoate (1.2 g, 7.6 mmoles), piperidine (6 drops) and hexanoic acid (8 drops) in dry benzene (80 ml) was heated at reflux 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 2.9 g.

Workup

  1. temperatureat reflux
  2. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-237a8a17b95a433a9d6231ded81408ce
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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