M-Butyryl chloride

In a 1-1. three-necked flask fitted with a Hershberg wire stirrer, a reflux condenser equipped with a calcium chloride drying tube, and a dropping funnel, are placed 237 g. (2.21 moles) of methyl-aniline (Note 5) and 300 ml. of dry benzene (Note 6). Stirring is started, and the reaction mixture is cooled in an ice-water bath during the dropwise addition of 197 g. (1.06 moles) of a-bromo-M-butyryl chloride diluted with approximately 40 ml. of dry benzene. The addition requires approximately 1 hour, and the reaction mixture becomes thick owing to the separation of methyl-... 

M-Butyryl chloride has been prepared from -butyric acid and phosphorus trichloride.1... 

Butyryl chloride (butanoyl chloride) [141-75-3] M 106.6, m -89°, b 101-102 /atm, d 1.026, Up 1.412. Check IR to see if there is a significant peak at 3000-3500 cm (br) for OH. If OH is present then reflux with less than one mol equiv of SOCI2 for Ih and distil directly. The fraction boiling between 85-100° is then refractionated at atm pressure. Keep all apparatus free from moisture and store the product in sealed glass ampoules under N2. LACHRYMATORY - handle in a good fume hood. [Org Synth Coll Vol I 147 1941]. 

Ethoxyphenyl Tellurium TVichloride To a vigorously boiling suspension of 9.0 g (30 mmol) 4-ethoxybenzene tellurinyl chloride in 50 m/ anhydrous carbon tetrachloride is added a solution of 6.4 g (60 mmol) butyryl chloride in 5 ml carbon tetrachloride. The refluxing mixture is stirred for 1 h. On cooling, 4-ethoxyphenyl tellurium trichloride precipitates. The precipitate is collected by filtration and recrystallized from acetic acid. The filtrate is stripped of the solvent and the residue distilled at atmospheric pressure. Butyric anhydride boiled at 198° yield 89%. 

Butyrylurea 621 A mixture of urea (10 g), benzene (25 ml), and a little concentrated sulfuric acid (2 drops) is boiled under reflux while butyryl chloride (15 g) is added with stirring during 15 min. The mixture is boiled for a further 4 h, then cooled. The acylated urea separates and is collected and washed with sodium hydrogen carbonate solution and with water, then having m.p. 173-174° (75-85%). 

M n-butyllithium in hexane added gradually to a vigorously stirred soln. of thioanisole and TMEDA in ether at —10° under N2, stirring continued at room temp, for 12 h, cooled to —80°, a soln. of butyryl chloride in ether added gradually over 30 min, the mixture stirred at —80° for 1 h, allowed to warm to room temp., stirred... 

Fluorosulfonic acid added drop wise with cooling and stirring at ca. —5° to n-butyric anhydride, and warmed slowly to room temp, under reduced pressure n-butyryl fluoride. Y ca. 95%. F. e., also carboxylic acid chlorides with chlorosulfonic acid, s. M. Schmidt and K. E. Pichl, B. 98, 1003 (1965). ... 

---