Benzoic anhydride hydrolysis

Propionic acid [79-09-4] M 74.1, b 141 , d 0.992, n 1.3865, n25 1.3843, pK 5-6.8 (Ho scale, aq H2SO4), pK2 4.88. Dried with Na2S04 or by fractional distn, then redistd after refluxing with a few crystals of KMn04. An alternative purification uses the conversion to the ethyl ester, fractional distn and hydrolysis. [Bradbury J Am Chem Soc 74 2709 1952.] Propionic acid can also be heated for 0.5h with an amount of benzoic anhydride equivalent to the amount of water present (in the presence of Cr03 as catalyst), followed by fractional distn. [Cham and Israel 7 C/iem 5oc 96 I960.]... 

Compared with esters, acid halides and anhydrides are more reactive and are hydrolyzed more readily. It is interesting to note that there is a substantial lifetime for these acid derivatives in aqueous media. Acid halides dissolved in PhCl or in PhBr shaken at a constant rate with water shows that hydrolysis occurs at the boundary between the two liquid phases.35 The reaction of benzoyl chloride (PhCOCl) and benzoate ion with pyridine A-oxide (PNO) as the inverse phase-transfer catalyst yields both the substitution product (benzoic anhydride) and the... 

Poly(methyl 3-(l-oxypyridinyl)siloxane) was synthesized and shown to have catalytic activity in transacylation reactions of carboxylic and phosphoric acid derivatives. 3-(Methyldichlorosilyl)pyridine (1) was made by metallation of 3-bromopyridine with n-BuLi followed by reaction with excess MeSiCl3. 1 was hydrolyzed in aqueous ammonia to give hydroxyl terminated poly(methyl 3-pyridinylsiloxane) (2) which was end-blocked to polymer 3 with (Me3Si)2NH and Me3SiCl. Polymer 3 was N-oxidized with m-ClC6H4C03H to give 4. Species 1-4 were characterized by IR and H NMR spectra. MS of 1 and thermal analysis (DSC and TGA) of 2-4 are discussed. 3-(Trimethylsilyl)-pyridine 1-oxide (6), l,3-dimethyl-l,3-bis-3-(l-oxypyridinyl) disiloxane (7) and 4 were effective catalysts for conversion of benzoyl chloride to benzoic anhydride in CH2Cl2/aqueous NaHCC>3 suspensions and for hydrolysis of diphenyl phosphorochloridate in aqueous NaHCC>3. The latter had a ti/2 of less than 10 min at 23°C. 

Oxygen can be introduced into the a-positions of thietanes by treatment of the thietane with lead tetraacetate as in the formation of (204) (75JOC3046). Thietanones can be prepared by hydrolysis of thiete enamines such as (205) (65LA(684)103) or by oxidation of 3-thietanol with DMSO/benzoic anhydride (78PS(4)167>. Thietanones can be converted into various ring-substituted sulfur derivatives as already illustrated in reactions of (68) and preparation of (199). 

Benzoic acid, 706,711, 752,755,756 Benzoic anhydride, 794 Benzoin, 708,714 Benzoin condensation, 708, 714 a-Benzoin oxime, 958 Benzonitrile, 609, 803 hydrolysis of, 609 ... 

Acetyl )thiooxindole may be prepared by fusing together thio-oxindole and A,A -diphenylacetamidine to give the anil (217), which affords the acetyl compound on alkaline hydrolysis.573 Acetylation and benzoylation of thiooxindole are possible by using mixtures of acetic anhydride and sodium acetate or benzoic anhydride and sodium benzoate, respectively.575... 

The use of benzoic anhydride with DMAP as a catalyst provides a convenient means for the preparation of the per-0-benzoylated derivatives of GSLs. These derivatives can subsequently be utilized for analytical and preparative HPLC because parent GSLs can be conveniently recovered in high yields by mild alkaline hydrolysis. 

Catalysis of the synthesis of benzoic anhydride and the hydrolysis of benzoyl chloride, diphenyl phosphorochloridate (DPPC), and benzoic isobutyric anhydride in dichloromethane-water suspensions by water-insoluble silanes and siloxanes, 3- and 4-trimethylsilylpyridine 1-oxide (3b and 3c, respectively), 1,3-bis(l-oxypyridin-3-yl)-l,1,3,3-tetramethyldisiloxane (4), and poly[methyl(l-oxypyridin-3-yl)-siloxane] (5) was compared with catalysis in the same systems by water-soluble pyridine 1-oxide (3a) and poly(4-vinylpyridine 1-oxide) (6). All catalysts were effective for anhydride synthesis and promoted the disproportionation of benzoic isobutyric anhydride. Hydrolysis of benzoyl chloride gave benzoic anhydride in high yield ( 80%) for all catalysts except 3a, which gave mixtures of anhydride (52%) and benzoic acid (39%). The order of catalytic activity for DPPC hydrolysis was 5 > 4 > 3b > 3a > 3c > 6. The results suggest that hydrophobic binding between catalyst and lipophilic substrate plays an important role in these processes. 

Hydrolysis of Benzoyl Chloride. Early experiments demonstrated that 3b, 3c, 4, and 5 are effective catalysts for the conversion of benzoyl chloride to benzoic anhydride in well-stirred suspensions of dichloro-methane-0.5 M aqueous sodium bicarbonate (equation 8) (2, 3). The results... 

Hydrolysis of Benzoic Isobutyric Anhydride. Reactions of mixed anhydrides can be complicated by disproportionation reactions (equation 10). The process may be operative in any investigation of anhydride hydrolysis, but it would go undetected in studies with symmetrical anhydrides or in studies that just monitor reaction rates by consumption of base. To obtain a more complete understanding of the catalytic behavior of 3, 4, 5, and 6 in transacylation reactions, the hydrolysis of benzoic isobutyric anhydride was investigated. 

These data are for the hydrolysis of substituted benzoic anhydrides in 75% dioKane. ... 

F) Preparation of Sulfonphthaleins. The preparations described involve (1) hydrolysis of o-sulfobenzoic imide (saccharin) to the ammonium salt of o-sulfobenzoic acid (2) preparation of o-sulfo-benzoic anhydride (3) preparation of phenolsulfonphthalein (phenol red) (4) bromination of phenolsulfonphthalein to tetrabromo derivative (bromophenol blue) (5) preparation of o-cresolsulfon-phthalein (cresol red) (6) bromination of o-cresolsulfonphthalein to the dibromo derivative (bromocresol purple)The equations for the steps are ... 

Carboxylic acid fluorides are not of particular preparative importance since the reactions that can be carried out with them proceed analogously with the cheaper carboxylic acid chlorides. These fluorides are very stable, even towards hydrolysis. Formyl fluoride can be kept at room temperature for several hours before it decomposes into CO and HF. The preparation of carboxylic acid fluorides from the corresponding chlorides and KF was mentioned on page 204. If butyric anhydride is heated gradually to 180° with KHF2, butyryl fluoride, b.p. 67° 1167 mm, distils off, and benzoyl fluoride, b.p. 155-156°, can be obtained analogously from benzoic anhydride at 190-240°. KF can also be used in place of KHF2. Yields are around 80-90%.1079... 

Yet a further method of cleaving acetals is to treat them with acid anhydrides, such as acetic or benzoic anhydride, in the presence of hydrogen ions 95 equimolar amounts of acetal and anhydride give the aldehyde and the ester. Oximes, hydrazones, and Schiff bases can be obtained directly on acid hydrolysis of acetals in the presence of, e.g.9 hydroxylamine, hydrazine, or amines, respectively. 

Indole is acetylated at position 3 by acetic anhydride without a catalyst when vinyl acetate is used as reaction medium.557 Heating benzanilide and benzoic anhydride with polyphosphoric acid for 3 hours at 150° leads, after hydrolysis, to an 84% yield of p-aminobenzophenone.558 Trifluoroacetylation of azulenes has been reported by Anderson and Anderson.559... 

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