Perkin reaction, synthesis

Kuhlberg, Ann. 163, 123 (1872) von Miller, Ann. 188, 196 0877). Synthesis (Perkin reaction) Irom benzaldehyde, aoe-tic anhydride, and potassium acetate Org. Reactions 1, 248 (1942) from oxalyl bromide + styrene Treibs et aL, NatUr-wiss. 45, 85 (1958) from acetylene + benzaldehyde Her-betz, Her. 92, 541 (1959). Prepn of cis- and traui-isomers Comte et at. Compt. Rend. 245, 1144 (1957). lsoln from wood-rotting fungus, Stereum subpileatum Berk. St Curt. Birkinshaw et at, Biochem. J. 66, 188 (1957). [Pg.358]

Paal-Knorr Pyrrole Synthesis Parham Cyclization Passerini Reaction Patemo-Biichi Reaction Pauson-Khand Reaction Payne Rearrangement Pechmann Condensation Pechmann Pyrazole Synthesis Pellizzari Reaction Pelouze Synthesis Periodic Acid Oxidation Perkin Alicyclic Synthesis Perkin Reaction Perkin Rearrangement Perkow Reaction Peterson Reaction... [Pg.12]

Chapter IV. a-Chloromethylnaphthalene (IV,23) benzylamine (Gabriel synthesis) (IV,39) i r.N -dialkylanilines (from amines and trialkyl orthophosphates) (IV,42) a-naphthaldehyde (Sommelet reaction) (IV,120) a-phenyl-cinnamic acid (Perkin reaction using triethylamine) (IV,124) p-nitrostyrene (IV,129) p-bromonaphthalene and p naphthoic acid (from 2 naphthylamine-1 -sulphonic acid) (IV,62 and IV,164) diphenic acid (from phenanthrene) (IV,165). [Pg.1191]

Manufacture. The most widely employed method for the commercial synthesis of (H)-cinnamic acid uti1i2es ben2aldehyde, acetic anhydride, and anhydrous sodium or potassium acetate in a condensation reaction commonly referred to as the Perkin reaction (11). [Pg.173]

Because of the mild reaction conditions, and its broad applicability, the Knoevenagel reaction is an important method for the synthesis of a ,/3-unsaturated carboxylic acids. Comparable methods are the Reformatsky reaction, the Perkin reaction, as well as the Claisen ester condensation. The Knoevenagel reaction is of greater versatility however the Reformatsky reaction permits the preparation of a ,/3-unsaturated carboxylic acids that are branched in a-position. [Pg.178]

A variant of the Perkin reaction is the Erlenmeyer-Plochl-azlactone synthesis By condensation of an aromatic aldehyde 1 with an N-acyl glycine 5 in the presence of sodium acetate and acetic anhydride, an azlactone 6 is obtained via the following mechanism ... [Pg.226]

Azlactones like 6 are mainly used as intermediates in the synthesis of a-amino acids and a-keto acids. The Erlenmeyer-Pldchl reaction takes place under milder conditions than the Perkin reaction. [Pg.226]

Palmitic acid, 69 o-Pelargonylphenol, 58 P-Pelaigonylphenol, 58 Pentaacetyl d-CLUcononitrile, 14,74 2,4-PENTANEDIONE, 6 Pentose synthesis, 14 Perkin reaction, 55 Peroxide, removal, 95 Perphthalic acid, mono-, 70... [Pg.57]

Ultra-violet absorption, 13, 132, 218 Umpolung, 211 Unsaturated acids afi-, from Perkin reaction, 227 j8y-, synthesis, 234... [Pg.214]

Perkin Reaction (Perkin cinnamic acid synthesis) The Reaction ... [Pg.492]

The analysis depicted for (64) reveals that the synthesis of benzofuran involves the conversion of salicylaldehyde into the corresponding aryloxyacetic acid by reaction with sodium chloroacetate in the presence of alkali, followed by heating with a mixture of acetic anhydride, acetic acid and sodium acetate (Expt 8.24). The ensuing cyclisation may be regarded as an internal Perkin reaction (Section 6.12.3, p. 1036) accompanied by a decarboxylative dehydration step. [Pg.1157]

Selenophene-2-aldehyde takes part in the Hantzsch synthesis [Eq. (I)]108 and reacts readily with ammonia, aromatic amines and diamines,109 hippuric, barbituric, and malonic acids, malononitrile,70 and rhodanine.109 /3-(Selenien-2-yl)acrylic acid has been obtained from selenophene-2-aldehyde by the Perkin reaction and by Knoevenagel condensation with malonic acid.70 Esters of /9-(selenien-2-yl)acrylic acid are easily formed by condensation of the aldehyde... [Pg.31]

In the Pschorr synthesis (Scheme 12.12), a Perkin reaction (see Chapter 6) between 2-nitrobenzaldehyde and sodium phenylacetate in the presence of acetic anhydride yields 3-(2-nitrophenyl)-2-phenyl-propenoic acid. Reduction of the nitro group and deamination of the resulting amine via its diazonium salt (see Chapter 8) is accompanied by cyclization. Thermal decarboxylation completes the sequence. [Pg.143]

Perkin Synthesis of Coumarin.—Coumaric acid and coumarin may be synthesized by the Perkin reaction for synthesizing unsaturated aromatic acids (p. 698). These syntheses are of historical interest as the two compounds obtained were the first onesprepared by this reaction. Instead of taking a simple aromatic aldehyde it is only necessary to take a phenol aldehyde viz., salicylic aldehyde,... [Pg.727]

Chapter 59 The Perkin Reaction Synthesis of a-Phenylcinnamic Acid... [Pg.491]

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