Benzaldehyde → HCID 12346449, compound

HRID 1941484Notes

Reaction equation

HRID 1941484 reaction equation
[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CSC.[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[N+]=[N-])[CH:16]=[CH:17][CH:18]=1>C([O-])(=O)C.[Rh+2].C([O-])(=O)C.ClCCl>[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]2[CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[O:8]2)[CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 1068Dimethyl SulfideHCID 21461373HCID 21461373, compound

Product 1

HCID 12346449HCID 12346449, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 21674Acetic acid, rhodium(2+) saltCatalystHCID 6344DichloromethaneSolvent

Procedure

To a slurry of rhodium (II) acetate (0.001 g) and dichloromethane (4 ml) were added benzaldehyde (0.025 ml) and dimethylsulphide (0.009 ml). The solution of 3-chlorophenyldiazomethane (produced above) was added to this mixture over 24 hours. The solvent was removed in vacuo and the residue chromatographed on silica (Merck grade 60, 230-400 mesh) eluting with dichloromethane:hexane 2:3 to give the title compound as a colourless oil (0.0305 g, 53% yield) δH (CDCl3): 7.55(8H); 7.45(1H), 4.0(2H)ppm.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue chromatographed on silica (Merck grade 60, 230-400 mesh)
  3. washeluting with dichloromethane:hexane 2:3

Sources & evidence

ORD record
ord-8dd5af15f0e74396b248ecc489dc46b9
Source dataset
uspto-grants-1997_12
Patent number
US05703246

Reaction notes

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