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

HRID 2210288Notes

Reaction equation

HRID 2210288 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C(N(CC)[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH3:23])=[O:16])C.C(O)(=O)C>[Pd]>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:13]=[CH:14][C:15]([O:17][CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH3:23])=[O:16])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 696764-IodoanisoleHCID 193802692-Ethylhexyl beta-diethylamino-propionate

Product 1

HCID 216302-Propenoic acid, 3-(4-methoxyphenyl)-, 2-ethylhexyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Conditions

Temperature
150 °C

Procedure

A mixture of 2.34 g (10 mmol) of p-iodoanisole, 2.57 g (10 mmol) of 2-ethylhexyl β-diethylamino-propionate, 0.9 g (15 mmol) of acetic acid and 15 mg of palladium on charcoal (5%) is stirred at 150° C. for 2 hours. Therafter, the mixture is worked up as in Example 1. 2-Ethylhexyl p-methoxycinnamate is obtained in 93% yield.

Sources & evidence

ORD record
ord-17ff5446d4d940539aada0ddc9da3d6a
Source dataset
uspto-grants-1995_10
Patent number
US05457226

Reaction notes

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