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

HRID 1741809Notes

Reaction equation

Br[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(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.BrC1C=CC=CC=1OC>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[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

Conditions

Temperature: 170 °C

Procedure

A reaction mixture of 18.7 g of 4-bromoanisole, 20.3 g of 2-ethylhexyl acrylate, 6.36 g of sodium carbonate, 0.0025 g of palladium(II) acetate, 0.21 g of triphenylphosphane and 5.0 g of polyethylene glycol 1000 was heated to 170° C. under nitrogen. The conversion of bromoanisole, determined by gas chromatography, was 100% after 2 hours. After vacuum distillation, an 82% yield of 2-ethylhexyl 4-methoxycinnamate, based on the 4-bromoanisole reacted, was obtained.

Workup

customafter 2 hours
distillationAfter vacuum distillation

Sources & evidence

ORD record: ord-b7e24a1e2a1b487e86c7370f07b16d00
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05334750

Reaction notes

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