2,3-Dichlorobenzaldehyde → (S)-2,2,2-Trichloro-1-phenylethyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate

HRID 1789021Notes

Reaction equation

HRID 1789021 reaction equation
[O:1]=[C:2]([CH3:18])[CH2:3][C:4]([O:6][C@@H:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([Cl:11])([Cl:10])[Cl:9])=[O:5].[Cl:19][C:20]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O>C1C=CC=CC=1.C(O)(=O)CCCCC.N1CCCCC1>[Cl:19][C:20]1[C:27]([Cl:28])=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=[C:3]([C:2](=[O:1])[CH3:18])[C:4]([O:6][C@@H:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([Cl:9])([Cl:10])[Cl:11])=[O:5]

Participants

6

Reactant 2

HCID 357452,3-DichlorobenzaldehydeHCID 54298419(S)-2,2,2-Trichloro-1-phenylethyl 3-oxobutanoate

Product 1

HCID 53903953(S)-2,2,2-Trichloro-1-phenylethyl 2-(2,3-dichlorophenylmethylene)-3-oxobutanoate

Reagents, catalysts & solvents 3

HCID 8082PiperidineCatalystHCID 8892Hexanoic AcidCatalystHCID 241BenzeneSolvent

Procedure

(S)-2,2,2-Trichloro-1-phenylethyl 3-oxobutanoate (8.6 g 27.5 mmoles) and 2,3-dichlorobenzaldehyde (4.82 g, 27.5 mmoles) in dry benzene (100 ml) were heated at reflux for 5 hours with hexanoic acid (25 drops) and piperidine (8 drops) in a Dean and Stark apparatus. The solvent was evaporated and the residue dissolved in ethyl acetate (200 ml), washed with saturated sodium bicarbonate, 2% aqueous sodium bisulphite solution and brine, dried (MgSO4) and the solvent removed in vacuo. The sub-title compound was obtained as a yellow oil. HPLC and nmr indicate 2:1 mixture of geometric isomers.

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue dissolved in ethyl acetate (200 ml)
  3. washwashed with saturated sodium bicarbonate, 2% aqueous sodium bisulphite solution and brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ec3d7272ec1a49eebd7fd4a8780aeecc
Source dataset
uspto-grants-1987_08
Patent number
US04686217

Reaction notes

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