Acrylic acid, methyl ester

Chemical Designations - Synonyms Acrylic acid, methyl ester Methyl 2-propenoate Chemical Formula CH2=CHCOOCH3. 

Eberle and Schaub (93EUP571326) describe the synthesis of a large series of 3-hydroxy-2-(2-methyl-4-prop-l-ynyl-2//-pyrazol-3-yl)acrylic acid methyl esters 26 and methoxyimino-(2-methyl-4-prop-l-ynyl-2//-pyrazol-3-yl)acetic acid methyl esters 27 by dehydrohalogenation of the corresponding chloroolefins 25 under the action of bases. In this case, the functional groups in position 5 of the pyrazole ring undergo dehydrobromination (Scheme 34). 

The 2-phenyl-2-ethyl-pentane-1,5-diacid-mononitrile-(1) of melting point 72° to 76°C, used as starting material in this process, can be produced for example from o-phenyl-butyric acid nitrile by condensation with acrylic acid methyl ester and subsequent hydrolysis of the thus-obtained 2-phenyl-2-ethyl-pentane-1,5-diacid-monomethyl ester-mononltrile-(l) of boiling point 176° to 185°C under 12 mm pressure. 

Triethylamine (8) Ethanamine, N,N-diethyl- (9) (121-44-8) Methyl acrylate Acrylic acid, methyl ester (8) 2-Propenoic acid, methyl ester (9) (96-33-3)... 

Fig. 6.7. Viscosity sensitive fluorophores molecular rotors. DCVJ = 9-(dicyanovinyl)-julolidine, CCVJ = 9-(carboxy-2-cyano)vinyl julolidine, CMAM = 2-cyano-3-(p-dimethyl-aminophenyl)acrylic acid, methyl ester.

Preliminary results from a study of catalytic activation of the heterocoupling between arylhalides and alkenes using pony-tail-functionalized dendrimer-encapsulated Pd nanoparticles have shown promise. For example, the classic Pd-catalyzed Heck coupling between arylhalides and methacrylate yields predominately (> 97%) the trans-cinnimaldehyde product [176]. On the other hand, the C02-soluble dendrimer nanocomposite exclusively catalyzes the production of the highly unfavored 2-phenyl-acrylic acid methyl ester isomer at 5000 psi and 75 °C (Fig. 27] [177]. 

Synonyms Acrylic acid, methyl ester AI3-15715 BRN 0605396 CCRIS 1839 Curithane 103 EINECS 202-500-6 Methoxycarbonylethene Methoxycarbonylethylene Methyl propenate Methyl propenoate Methyl-2-propenoate NSC 24146 Propenoic acid, methyl ester 2-Propenoic acid, methyl ester UN 1919. 

Synonyms 2-Propenoic acid methyl ester acrylic acid methyl ester methyl propenoate... 

Acrylic Acid, 2-Ethylhexyl Ester Acrylic Acid, Isobutyl Ester Acrylic Acid, Methyl Ester Acrylic Aldehyde Acrylic Amide, 50 %... 

METHYL ACRYLATE Acrylic Acid,methyl ester, Methyl 2-propenoate Flammable Liquid, 11 2 3 2 ... 

Fig. 16.35 (part I). Heck reaction of an aryl triflate with acrylic acid methyl ester under "classical," i.e., the Richard Heck conditions with a mechanistic analysis of the beginning of the reaction sequence, namely the formation of the catalytically active Pd(0) complex (= compound F). 

Step 5 of the mechanism shown in Figure 16.35 (part II) is new. It consists of the cw-selec-tive addition of the aryl-Pd complex to the C=C double bond of the acrylic acid methyl ester, i.e., a carbopalladation of this double bond. A related reaction, the cw-selective car-bocupratlon of C=C triple bonds, was mentioned in connection with Figure 16.17. The regioselectivity of the carbopalladation is such that the organic moiety is bonded to the methylene carbon and Pd to the methyne carbon of the reacting C=C double bond. The addition product is an alkyl-Pd(II) complex. 

A haloalkene that contains a stereogenic C=C double bond can usually be coupled with alkenes via the Heck reaction without isomerization. This is illustrated with the three reaction pairs in Figure 16.36. As can be seen, both the as- and the /raw-configured iodoalkenes react with acrolein or methyl vinyl ketone or acrylic acid methyl ester with complete retention of the C=C double bond configuration. These coupling reactions are thus stereoselective and— when considered as a pair—stereospecific. 

Steps 1-3 of the catalytic cycle correspond to various steps of other catalytic cycles already discussed in Chapter 13. Step 1 tt-complex formation by combination of the aryl triflate and a sufficiently valence-unsaturated and thus sufficiently reactive Pd(0) species. Step 2 oxi-dative addition of the aryl triflate to Pd with formation of a Cspi—Pd(II) bond. Steps 3a and 3b exchange of a PPh3 ligand by an acrylic acid methyl ester via a dissociation/addition mechanism. The newly entered acrylic acid ester is bound as a 77 complex. 

Fig. 13.26. Mechanism of a Heck coupling with acrylic acid methyl ester. The elementary steps 1-3 correspond to those in Figures 13.7 and 13.14, and the further course of the reaction is described in the text.

E)-3-Cyclopentyl-2-[3-fluoro-4-(5-methyl-tetrazol-l-yl)-phenyl]-acrylic acid methyl ester... 

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