Carboxylic acids ketones from

Iodine in functionalization of C 19 meth> 1 group of 3d acetoxy 20/3 hydroxy 5 pregnene 46, 58 Iron powder in preparation of ketones from carboxylic acids, 47, 75 Isobutene, 45, 49... [Pg.131]

Notable examples of general synthetic procedures in Volume 47 include the synthesis of aromatic aldehydes (from dichloro-methyl methyl ether), aliphatic aldehydes (from alkyl halides and trimethylamine oxide and by oxidation of alcohols using dimethyl sulfoxide, dicyclohexylcarbodiimide, and pyridinum trifluoro-acetate the latter method is particularly useful since the conditions are so mild), carbethoxycycloalkanones (from sodium hydride, diethyl carbonate, and the cycloalkanone), m-dialkylbenzenes (from the />-isomer by isomerization with hydrogen fluoride and boron trifluoride), and the deamination of amines (by conversion to the nitrosoamide and thermolysis to the ester). Other general methods are represented by the synthesis of 1 J-difluoroolefins (from sodium chlorodifluoroacetate, triphenyl phosphine, and an aldehyde or ketone), the nitration of aromatic rings (with ni-tronium tetrafluoroborate), the reductive methylation of aromatic nitro compounds (with formaldehyde and hydrogen), the synthesis of dialkyl ketones (from carboxylic acids and iron powder), and the preparation of 1-substituted cyclopropanols (from the condensation of a 1,3-dichloro-2-propanol derivative and ethyl-... [Pg.144]

SECONDARY AND TERTIARY ALKYL KETONES FROM CARBOXYLIC ACID CHLORIDES AND LITHIUM PHENYLTHIO(ALKYL)CUPRATE REAGENTS tert-BUTYL PHENYL KETONE... [Pg.122]

One reaction that is quite efficient for lithium reagents but poor for Grignard reagents is the synthesis of ketones from carboxylic acids.112 The success of the... [Pg.644]

METHYL KETONES FROM CARBOXYLIC ACIDS CYCLOHEXYL METHYL KETONE... [Pg.123]

One reaction that is quite efficient for lithium reagents but poor for Grignard reagents is the synthesis of ketones from carboxylic acids.91 The success of the reaction depends upon the stability of the dilithio adduct that is formed. This intermediate does not break down until hydrolysis, at which point the ketone is liberated. Some examples of this reaction are shown in Section C of Scheme 7.4. [Pg.453]

KETONES FROM CARBOXYLIC ACIDS AND GRIGNARD REAGENTS METHYL 6-OXODECANOATE (Oecanolc acid, 6-oxo-, nethyl ester]... [Pg.59]

KETONES FROM CARBOXYLIC ACIDS AND GRIGNARD REAGENTS ... [Pg.136]

Because of the toxicity of cadmium compounds two alternative methods for the preparation of ketones from carboxylic acid derivatives are worthy of attention. The first involves the reaction of organocopper reagents [formed from copper(i) iodide and an alkyllithium] with a carboxylic acid chloride.12 7a,b... [Pg.616]

Synthesis of aromatic ketones from carboxylic acid derivatives (Expts 6.126 and 6.127). [Pg.1005]

Ketones from Carboxylic Acids and Grlgnard Reagents Methyl 6-Oxodecanoate... [Pg.275]

Structure of the Carbonyl Group 817 18-3 Nomenclature of Ketones and Aldehydes 818 18-4 Physical Properties of Ketones and Aldehydes 820 18-5 Spectroscopy of Ketones and Aldehydes 822 18-6 Industrial Importance of Ketones and Aldehydes 828 18-7 Review of Syntheses of Ketones and Aldehydes 829 18-8 Synthesis of Ketones from Carboxylic Acids 833 18-9 Synthesis of Ketones and Aldehydes from Nitriles 833... [Pg.17]

Organolithium reagents can be used to synthesize ketones from carboxylic acids. Organolithiums are so reactive toward carbonyls that they attack the lithium salts of carboxylate anions to give dianions. Protonation of the dianion forms the hydrate of a ketone, which quickly loses water to give the ketone (see Section 18-13). [Pg.833]

Conductivity measurements have revealed that DMF and carboxylic acid chlorides form salt-like adducts (22) in an equilibrium reaction (equation 12). Such adducts can be prepared either from DMF and acid halides (chlorides and bromides) or from chloromethyleneiminium salts and salts of carboxylic acids. Acyloxyiminium salts (23) can be prepared in the pure state by reacting acid amides with carboxylic acid chlorides in the presence of silver trifluoromethanesulfonate (equation 13). Salts of type (24 equation 14) are regarded as being intermediates in the synthesis of ketones from carboxylic acids and Grignard reagents in the presence of a-chloroenamines as well as in the preparation of acyl halides (F, Cl, Br, I) by action of a-haloenamines on carboxylic acids. ... [Pg.493]

Fuson, R. C. Formation of aldehydes and ketones from carboxylic acids and their derivatives, in The Chemistry of the Carbonyl Group (ed. [Pg.685]

Ketones from carboxylic acids. In a procedure4 for the preparation of 4-heptanone, a mixture of 4 moles of n-butyric acid and 2.2 moles of iron powder (Fisher) is refluxed for 5 hrs. under nitrogen, and then distilled. [Pg.391]

Methyl ketones from carboxylic acid chlorides.13 The reagent, 3 moles, prepared in ether solution, reacts with acid chlorides (1 mole) at —78° in 15 minutes to give the corresponding methyl ketones in excellent yield. The acid chloride can be... [Pg.59]

Ketones from carboxylic acid chlorides COC1 —COR... [Pg.219]

Ketones from carboxylic acids RCOOH + HOOCR —> R.R ... [Pg.229]

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