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

HRID 2210286Notes

Reaction equation

HRID 2210286 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].C(N(CC)CC)C.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C>[Pd].C1(C)C=CC=CC=1.O>[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

9

Reactant 5

HCID 297MethaneHCID 76362-Ethylhexyl acrylateHCID 8471TriethylamineHCID 696764-IodoanisoleHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl ester

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 4.68 g (20 mmol) of p-iodoanisole, 4.05 g (22 mmol) of 2-ethylhexyl acrylate, 2.22 g (22 mmol) of triethylamine, 1.32 g (22 mmol) of acetic add and 15 mg of palladium of charcoal (5%) is stirred at 150° C. After one hour it is established by gas chromatography that the reaction has been completed. The mixture is then treated at about 80° C. with water and toluene and the catalyst is filtered off. The organic phase is washed in sequence with 2N hydrochloric acid and water, dried over anhydrous sodium sulphate and concentrated under reduced pressure. After distillation there is obtained pure 2-ethylhexyl p-methoxycinnamate, b.p. about 185° C./0.3 Torr. The yield is 92% of theory. 1H-NMR (CDCl3, 200 MHz): 0.86-0.98 ppm (m, 6H), 1.25-1.72 ppm (m, 9H), 3.84 ppm (s, 3H), 4.11 ppm (d, 6 Hz, 2H), 6.32 ppm (d, 15.5 Hz, 1H), 6.85-6.95 ppm (duplettoid m, 1H), 7.44-7.54 ppm (duplettoid m, 1H), 7.64 ppm (d, 15.5 HZ, 1H).

Workup

  1. additionadd
  2. filtrationthe catalyst is filtered off
  3. washThe organic phase is washed in sequence with 2N hydrochloric acid and water
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. distillationAfter distillation

Sources & evidence

ORD record
ord-6253372d5fb14d71bf8abab2bc582e4f
Source dataset
uspto-grants-1995_10
Patent number
US05457226

Reaction notes

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