Acetic anhydride-Acetyl chloride

Pungent odour. Formic acid, acetic acid, acetyl chloride, acetic anhydride, benzoyl chloride, benzyl chloride, pyridine. Benzoquinone (when warmed with water). 

By dehydration with acetyl chloride, acetic anhydride or with phosphotus oxychloride, for example ... 

Friedel-Crafts Acylation. The Friedel-Crafts acylation procedure is the most important method for preparing aromatic ketones and thein derivatives. Acetyl chloride (acetic anhydride) reacts with benzene ia the presence of aluminum chloride or acid catalysts to produce acetophenone [98-86-2], CgHgO (1-phenylethanone). Benzene can also be condensed with dicarboxyHc acid anhydrides to yield benzoyl derivatives of carboxyHc acids. These benzoyl derivatives are often used for constmcting polycycHc molecules (Haworth reaction). For example, benzene reacts with succinic anhydride ia the presence of aluminum chloride to produce P-benzoylpropionic acid [2051-95-8] which is converted iato a-tetralone [529-34-0] (30). 

Enol esterification with acetyl chloride-acetic anhydride gives the A -trien-3-acetate, but reaction with isopropenyl acetate or with hot acetic anhydride-pyridine gives A " -trien-3-acetates. " Since A"" -3-ketones react with Girard reagents, these linear dienones can be separated from A ""-3-ketones. ... 

Self-condensation of the substituted propiophenone, 15, by the pinacol reaction proceeds to give the glycol, 16, as the meso isomer. (If it is assumed that the transition state for this reaction resembles product, this stereoselectivity can be rationalized on the grounds of steric interaction compare A, which leads to the observed product, with B.) Dehydration under very specialized conditions (acetyl chloride, acetic anhydride) affords the bisstyrene-type diene (17). Removal of the acyl groups by means of base affords the synthetic estrogen, dien-... 

Hydroxyl endgroups are usually titrated by acetylation or phthalylation in pyridine using an excess acetyl chloride, acetic anhydride, or phthalic anhydride. The excess of reactant is hydrolyzed and back titrated by aqueous sodium or potassium hydroxide. 

Bromine-chlorine exchange with pyrazolotropones is rapid in the case of dibromide 142 [by HCl/methanol, substitution of one bromine atom (66BCJ253)], but exchange proceeds slowly and incompletely with a 5-bromo compound [by acetyl chloride/acetic anhydride (61MI2)]. 

The reactivity of A2-thiazolin-5-ones is closely related to the protomeric equilibrium shown in Scheme 127. The nucleophilic activity of the C-5 oxygen atom is clearly demonstrated by its reaction with acetyl chloride, acetic anhydride, benzoyl chloride, methyl or phenyl isocyanate, carbamoyl chloride or phosphorus derivatives in the presence of bases, to give (205-208 Scheme 140). 

The Te = N bond in diaryl tellurium sulfonimides is cleaved by boiling water, by boiling aqueous solutions of alkali hydroxides, by dry hydrogen chloride2, acetyl chloride, acetic anhydride or acetic acid in chloroform3. 

ACETAMIDE ACETANILIDE ACETYL CHLORIDE ACETIC ANHYDRIDE DIMETHYL ACETAMIDE CELLULOSE ACETATES ESTERS... 

N 19.17% oil, ftp 1.0-1.6° bp 103-04°at lOmm press, n 1.4559 at 20° stable in 70% sulfuric acid at 25° It was prepd by nitrating di-n-propylamine with 99% nitric acid in the presence of acetyl chloride acetic anhydride in glac acet ac (Refs 1 2)... 

The a proton of a substituted cyclopropane is also rendered acidic if the substituent is attached to the ring by C-P bonds. A few reports have appeared on a-substitution in such compounds.(Cyclopropyl)triphenylphosphonium bromide was converted to a (1-ethoxy-carbonylcyclopropyl)triphenylphosphonium salt 18 in 80% yield by sequential treatment with lithium diisopropylamide and ethyl chloroformate. Furthermore, some diethyl cyclopropyl-phosphonates were converted, in some cases in excellent yield, to diethyl (1-hydroxymethyl-cyclopropyl)phosphonates by treatment with lithium diisopropylamide followed by addition of an aldehyde." Thus, typically, diethyl 2-hexylcyclopropylphosphonate gave diethyl 2-hexyl-l-[hydroxy(phenyl)methyl] cyclopropylphosphonate (19b) in 90% yield on reaction with benzaldehyde. ° Other electrophiles such as acetone, acetyl chloride, acetic anhydride, and ethyl acetate, were not sufficiently reactive to undergo addition to the anion. 

Figure 20.1 shows the structures and electrostatic potentials of the various derivatives of acetic acid-acetyl chloride, acetic anhydride, ethyl acetate, acetamide, and acetonitrile. Like the other carbonyl-containing compounds that we ve studied, acyl chlorides, anhydrides, esters, and amides all have a planar arrangement of bonds to the carbonyl group. 

Ci2H10O, Mr 170.21, 6pi.7kPa 171-173 °C, df 1.171, ng° 1.6752, has been identified in some essential oils. It smells like orange blossom and is a colorless crystalline solid (mp 56 °C). It is usually prepared by Friedel-Crafts acetylation of naphthalene (with acetyl chloride, acetic anhydride, etc.) in the presence of aluminum chloride. In polar solvents (e.g., nitrobenzene), the percentage of the simultaneously formed a isomer is lower. Methyl P-naphthyl ketone is used in eau de cologne, soap perfumes, and detergents. It is a good fixative. 

The solid cobalt(III) complex was refluxed with benzoyl chloride, acetyl chloride, acetic anhydride, phosphorus tribromide, or thionyl chloride. In none of these cases was there any evidence that a reaction had occurred. Prolonged refluxing with concentrated HC1 gave no reaction... 

Oxidation of solasodine (6) with oxygen has given the keto-acid (7), which was lactonized by heating in acetyl chloride-acetic anhydride, to yield (8). ... 

Also obtained by acetylation of resorcinol monomethyl ether by treatment with complex mixture (acetyl chloride/acetic anhydride/acetic acid/anisole/sodium... 

A soln. of the startg. dienone in acetyl chloride, acetic anhydride, and pyridine refluxed 2.25 hrs. trienol acetate (Y 58.5%) refluxed 10 min. with NaHGOg in dry methanol crude product (Y 77.6% based on UV-spectrum). F. e. s. J. F. Bagli et al., Tetrah. Let. 196A, 387. 

---