Abstract
[108-24-7] C4H6O3 (MW 102.09)
InChI = 1S/C4H6O3/c1-3(5)7-4(2)6/h1-2H3
InChIKey = WFDIJRYMOXRFFG-UHFFFAOYSA-N
(useful for the acetylation of alcohols,2 amines,3 and thiols,4 oxidation of alcohols,5 dehydration,6 Pummerer7 reaction, Perkin8 reaction, Polonovski9 reaction, N-oxide reaction,10 Thiele11 reaction, ether cleavage,12 enol acetate formation,13 gem-diacetate formation14)
Physical Data: bp 138–140 °C; mp −73 °C; d 1.082 g cm−3.
Solubility: sol most organic solvents. Reacts with water rapidly and alcohol solvents slowly.
Form Supplied in: commercially available in 98% and 99+% purities. Acetic anhydride-d6 is also commercially available.
Analysis of Reagent Purity: IR, NMR.15
Preparative Methods: acetic anhydride is prepared industrially by the acylation of Acetic Acid with Ketene.1b A laboratory preparation of acetic anhydride involves the reaction of sodium acetate and Acetyl Chloride followed by fractional distillation.16
Purification: adequate purification is readily achieved by fractional distillation. Acetic acid, if present, can be removed by refluxing with CaC2 or with coarse magnesium filings at 80–90 °C for 5 days. Drying and acid removal can be achieved by azeotropic distillation with toluene.17
Handling, Storage, and Precautions: acetic anhydride is corrosive and a lachrymator and should be handled in a fume hood.
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