Acrylic Acid → HCID 59164601, compound

HRID 1441682Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([CH3:10])[CH:3]=1.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.[C:33]([OH:37])(=[O:36])[CH:34]=[CH2:35].C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[C:6]([C:5]1[CH:8]=[CH:9][C:2](/[CH:35]=[CH:34]/[C:33]([OH:37])=[O:36])=[CH:3][C:4]=1[CH3:10])#[N:7]

Participants

Conditions

Temperature: 200 °C

Procedure

9.0 g 4-bromo-2-methylbenzonitrile, 2.76 g tri-o-tolylphosphine, 3.11 ml acrylic acid and 25.1 ml triethylamine are dissolved in 80 ml acetonitrile. The reaction mixture is degassed, then 2.0 g palladium (II)acetate were added and the mixture stirred two hours under microwave irradiation at 200° C. The cooled reaction mixture was diluted by addition of 50 ml ethyl acetate. Thereby (E)-3-(4-Cyano-3-methyl-phenyl)-acrylic acid precipitated as a white solid. The precipitate was filtered off and dried in vacuo to obtain 2.5 g (E)-3-(4-Cyano-3-methyl-phenyl)-acrylic acid. The filtrate was washed with 1N HCl, thereby (E)-3-(4-Cyano-3-methyl-phenyl)-acrylic acid precipitated again as a white solid. The precipitate was filtered off and dried in vacuo to obtain 2.0 g (E)-3-(4-Cyano-3-methyl-phenyl)-acrylic acid. The filtrate was reduced in vacuo to one third of its volume, 150 ml diethyl ether were added, thereby (E)-3-(4-Cyano-3-methyl-phenyl)-acrylic acid precipitated again as a white solid. The precipitate was filtered off and dried in vacuo to obtain 840 mg (E)-3-(4-Cyano-3-methyl-phenyl)-acrylic acid

Workup

customThe reaction mixture is degassed
addition2.0 g palladium (II)acetate were added
customThe cooled reaction mixture
customThereby (E)-3-(4-Cyano-3-methyl-phenyl)-acrylic acid precipitated as a white solid
filtrationThe precipitate was filtered off
customdried in vacuo

Sources & evidence

ORD record: ord-7c97c943527a4f10839288aad1e00ec1
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655679B2

Reaction notes

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