Tributylamine → Benzenepropanal

HRID 1834484Notes

Reaction equation

HRID 1834484 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(N(CCCC)CCCC)CCC.CCCCCCCCCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:2]1([CH2:10][CH2:9][CH:8]=[O:11])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7622TributylamineHCID 7858Allyl AlcoholHCID 11575Iodobenzene2×HCID 12388Tridecane

Product 1

HCID 7707BenzenepropanalYield 62%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7583Diphenyl EtherSolvent

Procedure

0.1 g Palladium acetate, 10.2 g iodobenzene, 4.4 g allyl alcohol, 9.3 g tributylamine were heated together with 20 ml diphenyl ether as solvent and 2 g tridecane as internal standard. After 45 minutes at 135° the iodobenzene was 91% reacted to produce 62% 3-phenylpropanal and 13% hydratropic aldehyde based on conversion.

Workup

  1. custom91% reacted

Sources & evidence

ORD record
ord-8403b14b0c2c43eeb5af9b661f6d16bf
Source dataset
uspto-grants-1978_01
Patent number
US04070374

Reaction notes

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