Benzene → Ethyl Propionate

HRID 1180723Notes

Reaction equation

HRID 1180723 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].N#N.[CH:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[C:1]([O:5][CH2:6][CH3:7])(=[O:4])/[CH:2]=[CH:3]/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 241BenzeneHCID 947NitrogenHCID 8821Ethyl Acrylate

Product 2

HCID 7749Ethyl PropionateYield 26%HCID 637758Ethyl CinnamateYield 22%

Conditions

Temperature
180 °C

Procedure

A solution containing 8 ml of benzene, 0.02 mmol of [η6-C6H6—Ru(H2O)3](F3CSO3)2 and 5 mmol of ethyl acrylate in a Fisher-Porter glass reactor was pressurized with 1 atm CO and 7.1 atm of inert gas (e.g., Argon or N2) and heated to 180° C. with stirring for 48 hours. GC analysis revealed formation of 1.1 mmol (E)-ethyl cinnamate (22% yield, 55 TON) and 1.3 mmol ethyl propanoate (26% yield, 65 TON).

Sources & evidence

ORD record
ord-cadc6a1ecd67423eb999f09903c5cda2
Source dataset
uspto-grants-2007_10
Patent number
US07282618B2

Reaction notes

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