Quinoline → 4-Methylbenzaldehyde

HRID 1733180Notes

Reaction equation

HRID 1733180 reaction equation
[C:1]1([CH3:13])[CH:6]=[CH:5][C:4]([CH2:7]COC(=O)[O-])=[CH:3][CH:2]=1.[S].N1C2C(=CC=CC=2)C=CC=1.[O:25]1CCCC1>[Pd]>[CH3:13][C:1]1[CH:2]=[CH:3][C:4]([CH:7]=[O:25])=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 7047QuinolineHCID 8028TetrahydrofuranHCID 5362487SulfurHCID 86737396HCID 86737396, compound

Product 1

HCID 77254-MethylbenzaldehydeYield 88%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution containing 20.8 g (0.10 moles) of p-toluylethyl-carbonate in 300 ml of tetrahydrofuran there are added 10.4 g of Pd on BaSO4 10% and 0.1 cc of a solution of sulfur and quinoline 1:3000. Proceeding as in Example I, step (6), 10.5 g of p-methylbenzaldehyde (yield 88%) are obtained.

Sources & evidence

ORD record
ord-d19e8a266681448198d8f46c9b5a96ba
Source dataset
uspto-grants-1980_12
Patent number
US04240984

Reaction notes

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