Allyl Alcohol → Benzenepropanal

HRID 1834483Notes

Reaction equation

HRID 1834483 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([OH:11])[CH:9]=[CH2:10]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(N(CC)CC)C>[C:2]1([CH2:10][CH2:9][CH:8]=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7858Allyl AlcoholHCID 11575Iodobenzene2×

Product 1

HCID 7707BenzenepropanalYield 27%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
100 °C

Procedure

0.1 g Palladium acetate, 10.2 g iodobenzene, 4.4 g allyl alcohol and 6.0 g triethylamine were heated while stirring under nitrogen to 100° C. After one hour the iodobenzene was 97% reacted and there was produced 27% 3-phenylpropanal and 13% hydratropic aldehyde.

Workup

  1. custom97% reacted

Sources & evidence

ORD record
ord-30a15c62775045e3925b982a20bb6e92
Source dataset
uspto-grants-1978_01
Patent number
US04070374

Reaction notes

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