Tributylamine → Ethyl 3-(4-nitrophenyl)-2-propenoate

HRID 1156459Notes

Reaction equation

HRID 1156459 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:13]([O:17][CH2:18][CH3:19])(=[O:16])[CH:14]=C.C(N(CCCC)CCCC)CCC>CC1C=CC(C)=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH:8]=[CH:14][C:13]([O:17][CH2:18][CH3:19])=[O:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 7622TributylamineHCID 85024-Nitrobenzoyl chlorideHCID 8821Ethyl Acrylate

Product 1

HCID 95370Ethyl 3-(4-nitrophenyl)-2-propenoateYield 55.2%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 7809P-XyleneSolvent

Procedure

The procedure described in Example 1 is repeated, except that 9.28 g (0.05 mol) of 4-nitrobenzoyl chloride, 6.25 g (0.0625 mol) of ethyl acrylate, 8.65 g (0.05 mol) of tri-n-butylamine and 0.1122 g (0.0005 mol) of palladium acetate are used. After a reaction time of 1 hour at 120° C. in 100 ml of p-xylene as the solvent, 6.1 g (0.0276 mol) of ethyl 4-nitrocinnamate are obtained, corresponding to a yield of 55.2% of theory; melting point 137.5° C. Analysis for C11H11NO4 (molecular weight 221: calculated C 59.73%, H 5.01%, N 6.33%; found C 59.47%, H 4.96%, N 6.27%.

Sources & evidence

ORD record
ord-7d3bdad51ee74958aaa38a7dbcdc1ea8
Source dataset
uspto-grants-1982_06
Patent number
US04335054

Reaction notes

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