Acetic Acid → 2-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl ester

HRID 2210287Notes

Reaction equation

HRID 2210287 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[C:10]([O:14][CH2:15][CH:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])(=[O:13])[CH:11]=[CH2:12].CC(N)(C)CC(C)(C)C.C(O)(=O)C>[Pd]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:12]=[CH:11][C:10]([O:14][CH2:15][CH:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19][CH3:20])=[O:13])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 76362-Ethylhexyl acrylateHCID 61017tert-OctylamineHCID 696764-Iodoanisole

Product 1

HCID 216302-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl esterYield 92%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of 4.68 g (20 mmol) of p-iodoanisole, 4.05 g (22 mmol) of 2-ethylhexyl acrylate, 2.84 g (22 mmol) of 1,1,3,3-tetramethylbutylamine, 1.32 g (22 mmol) of acetic acid and 32 mg of palladium on charcoal (5%) is stirred at 150° C. for 3 hours. After working up as in Example 1 there is obtained 2-ethylhexyl p-methoxycinnamate in 92% yield.

Sources & evidence

ORD record
ord-94d19c1a66ae41b094f1b3d61bb9a886
Source dataset
uspto-grants-1995_10
Patent number
US05457226

Reaction notes

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