Acrolein diethyl acetal

We have shown that the direct arylation of acrolein toward the synthesis of cinnamaldehyde derivatives was an efficient procedure. Using the palladacycle 1 as catalyst, substituted aldehydes 3 were prepared with up to 87% isolated yield from condensed aiyl bromides (Scheme 21.1, Route 1) that was extended successfully to heteroaiyl bromides, like bromoquinolines (6). Alternatively, the acrolein diethyl acetal was used as olefin and a selective formation of the saturated ester 4 was attained under the same reaction conditions (Scheme 21.1, Route 2). The expected aldehydes 3 were, however, obtained from most of the aiyl halides used under modified conditions. It was shown that the addition of n-Bu4NOAc in the medium... 

Aconitic acid, p206 Acrolein, p203 Acrolein diethyl acetal, d312 Acrolein dimethyl acetal, d521 Acrylaldehyde, p203... 

A completely different approach to lithium homoenolate synthons uses a carbon-oxygen bond cleavage. Lithiation of acrolein diethyl acetal 180 with lithium and a catalytic amount of DTBB (2.5%) in the presence of different carbonyl compounds in THF at 0°C gave, after final hydrolysis, the corresponding y-products 181 in different diastereomeric ratios (Z/ 3/1 to 20/1) (Scheme 63) . 

The reaction of indolizines with aldehydes and ketones in the presence of acids yields coloured salts, two of which (43 and 44) are given here for illustration. The salts (45) and (46) have been obtained from the reaction of the pertinent indolizines with formaldehyde and glyoxal respectively. Polymethine dyes, some of which have found application in photography, have been prepared from indolizines and malondialdehyde derivatives or vinylogous dialdehydes (47) was prepared from 1,2-dimethylindolizine and /3-ethoxy-acrolein diethyl acetal (48). 

Acrolein, diethyl acetal, and propionaldehyde, P-ethoxy-, diethyl acetal)... 

Acidolysis of vinyl acetate by fatty adds, 30, 106 Acrolein acetal, 32, 5 Acrolein diethyl acetal, 32, 5 Acrylic acid, frans-/3-( -NiTROpHE. NYL)-a-PHENYL-, 35, 89 Acrylonitrile, 30, 80 Acrylonitrile, triphenyl-, 31, 52 Acylation of ethanolamine with phthalic anhydride, 32, 19... 

A- Acetylsulfanilyl chloride, alO Acrolein diethyl acetal, d258 1-Adamantanemethylamine, a209 ... 

A dimeric 4-hydroxyacetophenone oxime-derived palladacycle was used by Najera et al. as a very efficient precatalyst for selective and microwave-assisted arylations of acrolein diethyl acetal, furnishing 3-arylpropanoate products [45]. In the presence of Cy2NMe and tetrabutylammonium bromide (TBAB), higher reaction rates and slightly improved yields were realized under microwave conditions (Scheme 7). 

Scheme 2 The Heck reaction of 4-bromotoluene with acrolein diethyl acetal as followed using 79Br NMR spectroscopy. Adapted from Chan et al.30...

CROLEIN ACETAL, 32, 5 Acrolein diethyl acetal, 32, 5 crylic ACID, Irans 0 (o NITRO... 

Acetals and ketals having a second junctional group ate made by these procedures. For example, acrolein reacts with ethyl orthoformate in alcohol solution with ammonium nitrate as catalyst to give acrolein diethyl acetal (73%). On the other hand, it reacts with ethyl ortho silicate with anhydrous hydrogen chloride as catalyst to furnish (i-ethoxypropionaldehyde diethyl acetal (76%). p-Bromoacetophenone and ethyl orthoformate give the corresponding ketal in 65% yield. p-Methoxy- and m-amino-benzaldehyde diethyl acetals are made in a similar way in 96% and 85% yields, respectively. a-Keto esters like ethyl a-keto-n-butytate and ethyl a-keto-tr-valetate are converted to their diethyl ketals in excellent yields by the action of orthoformic ester in ethanol-hydrochloric acid solution. If the reaction is carried out in the presence of ethylene glycol instead of ethanol and, in addition, the volatile products are removed by distillation, then the ethylene ketal is formed in almost quantitative yield (cf. method 133). 

Unsaturated acetals can be prepared by the acetalization of an unsaturated aldehyde. Acrolein diethyl acetal, CHj=CH — CH(OCHjCH,)j, is prepared in this manner and also by the dehydrohalogenation of /3-chlo-ropropionaldehyde diethyl acetal (cf. method 20) however, the former method has definite advantages in that it involves a single-step process and gives a more stable product. The double bond may also be in the alcohol fragment, as In acetaldehyde diallyl acetal,... 

The treatment of acrolein diethyl acetal with potassium permanganate... 

Under conditions similar to those under which cyclohexene affords cis-cyclo-hexane-l,2-diol in yield of 30-33%, Evans et obtained DL-glyceraldehyde diethyl acetal from acrolein diethyl acetal in 67% yield. A suspension of the acetal... 

Acrolein diethyl acetal (3,3-diethoxy-I-propene or l,l-diethoxy2-propene) [3054-95-3] M... 

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