Benzene → 2,4-Dimethyl-3-phenyl-4-pentenal

Reaction equation

C([O:4][CH2:5]/[C:6](/[CH3:14])=[CH:7]/[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)C=C.[CH:15]1[CH:20]=CC=C[CH:16]=1>>[CH3:14][CH:6]([CH:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:15]([CH3:20])=[CH2:16])[CH:5]=[O:4]

Participants

Reactant 2

HCID 241Benzene

HCID 67330776(1E)-[3-(allyloxy)-2-methyl-1-propenyl]benzene

Product 1

HCID 584354742,4-Dimethyl-3-phenyl-4-pentenalYield 80%

Procedure

The (1E)-[3-(allyloxy)-2-methyl-1-propenyl]benzene (107.79 g, 0.571 mol), [RuCl2(PPh3)3] (3.13 g), BHT (1 g) and benzene (500 ml) were heated together in an autoclave in an oil bath at 190° C. for 4 hours. After cooling to room temperature, solvents were evaporated and the residue was distilled trough a 20-cm Widmer column to give 85.9 g of the desired compound (0.457 mol, 80%) as a 3:1 mixture of diastereoisomers. B.P.=95° C./0.032 mbar

Workup

customsolvents were evaporated
distillationthe residue was distilled trough a 20-cm Widmer column

Sources & evidence

ORD record: ord-ee942a59a0814da7a419c1f7c8745cf8
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08268895B2

Reaction notes

Loading…