Benzene → Propanal

HRID 460945Notes

Reaction equation

HRID 460945 reaction equation
[C:1]([O-:4])(=O)[CH3:2].[C:5]([O-])(=O)C.[C:9]([O-:12])(=[O:11])[CH3:10].[C:13]([O-:16])(=O)[CH3:14].[Pb+4].[CH:18]1C=CC=CC=1.C(O)(=O)C=O>O>[CH:1](=[O:4])[CH2:2][CH3:5].[CH:13](/[C:14](/[CH3:18])=[CH:10]\[C:9]([OH:12])=[O:11])=[O:16]

Participants

6

Reactant 3

HCID 241BenzeneHCID 760Glyoxylic AcidHCID 178418268HCID 178418268, compound

Product 2

HCID 527PropanalHCID 1778663970143-04-3

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Compounds of formula III where n is zero and B is an oxo group can be prepared, for example, by oxidatively cleaving an optionally esterified tartaric acid; for example, using lead tetraacetate at room temperature in an organic solvent such as benzene. The resulting glyoxalic acid derivative is subsequently condensed in a conventional manner, e.g., conveniently in the presence of an amine, with propionaldehyde at an elevated temperature, e.g., at a temperature between 60° C. and 110° C. with water cleavage to yield the corresponding 3-formyl-crotonic acid derivative.

Workup

  1. customat room temperature
  2. customcondensed in a conventional manner, e.g.

Sources & evidence

ORD record
ord-0dee54d2f1b3452da1c8f8b876211473
Source dataset
uspto-grants-1977_12
Patent number
US04061656

Reaction notes

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