Butyryl chloride


Prepare n-heptoyl chloride from the acid by treatment with thionyl chloride as detailed for n-butyryl chloride (Section 111,87) b.p. 173-175°.  [c.375]

Equip a 1500 ml. three-necked flask with an efficient mercury-sealed stirrer, a separatory funnel protected by a calcium chloride (or cotton wool) tube, and a double surface reflux condenser attached to a gas absorption device (Fig. 77, 8, 1, c). Weigh out 140 g. of finely-powdered, anhydrous aluminium chloride under sodium-dried A.R. benzene, and transfer the sohd to the flask already containing 231 g. (263 ml.) of anhydrous A.R. benzene. Place 105 g. (102 ml.) of n-butyryl chloride, b.p. 100-102° (Section 111,87) in the separatory funnel, run in 3-4 ml. into the flask and stir vigorously. Warm the flask gently to start the reaction (. c., until hydrogen chloride is evolved), remove the source of heat, and continue the addition during 2 hours. The reaction mixture darkens considerably. Reflux for 30 minutes to complete the reaction and allow to cool. Transfer the reaction mixture to a large separatory funnel and allow it to drip into about 2 litres of cold water in a 4-litre beaker, cooled externally in an ice bath, and vigorously agitated with an efficient mechanical stirrer. Separate the upper oily layer, wash it with 10 per cent, sodium hydroxide solution, then with water, and dry over anhydrous magnesium sulphate. Remove the benzene (Fig. 77, 75, 4, but use a 150 ml. Claisen flask), and distil the residue through an air condenser from an air bath. Collect the butyrophenone (a colourless liquid) at 227-230°. The yield is 75 g.  [c.732]

Several methods are available to supplement the phenol alkylations described above. Primary alkylphenols can be produced using the more traditional Friedel-Crafts reaction. Thus an -butylphenol can be synthesized direcdy from a butyl haUde, phenol, and mild Lewis acid catalyst. Alternatively, butyryl chloride can be used to acylate phenol producing a butyrophenone. Reduction with hydrazine (a Wolff-Kishner reduction) generates butylphenol.  [c.59]

Dichlorophenoxyacetic acid n-Butyryl chloride  [c.581]

The 2,3-dichlorophenoxyacetic acid and n-butyryl chloride are placed in the reaction vessel and stirred while the aluminum chloride is added portionwise over a 45-minute period. The mixture then is heated on the steam bath for 3 hours and allowed to cool to room temperature. The gummy product obtained is added to a mixture of 300 ml of crushed ice and 30 ml concentrated hydrochloric acid. The resulting mixture is extracted with ether and the extract evaporated at reduced pressure. The residue Is suspended in boiling water and dissolved by addition of a minimum quantity of 40% sodium hydroxide. After treatment with decolorizing charcoal and filtering, the hot filtrate is made acid to Congo red paper and chilled in ice.  [c.581]

Methohexital sodium Butyramidophenol Acebutolol Butyric anhydride lopanoic acid Tyropanoate sodium n-Butyryl chloride Ethacrynic acid  [c.1619]

This technique can be applied to prepare DL-a-fluoromethylputrescme (5-fluoropentane 1,4-diamine), a potent irreversible inhibitor of E colt ornithine decarboxylase, from 4-phthalimido-l -butyryl chloride, diazomethane, and hydro gen fluonde-pyridine [94 95]  [c.283]

The initial series of major tranquilizers consists of alkylated derivatives of 4-aryl-4-hydroxypiperidines. Construction of this ring system is accomplished by a set of rather unusual reactions. Condensation of methylstyrenes with formaldehyde and ammonium chloride afford the corresponding hexahydro-1,3-oxazines (119). Heating these oxazines in the presence of acid leads to rearrangement with loss of water to the tetrahydropyridines. Scheme 1 shows a possible reaction pathway for these transformations. Addition of hydrogen bromide affords the expected 4-bromo compound (121). This last is easily displaced by water to lead to the desired alcohol (122) The side chain (123) is obtained by Friedel-Crafts acylation of p-fluorobenzene with 4-chloro-butyryl chloride. Alkylation of the appropriate arylpiperidinol with 123 affords the desired butyrophenone derivative. Thus,  [c.306]

Geranyl Butyrate.—This ester of the formula Cj Hj,. OOC(CH2)2CHj is an oil having a fine rose odour, distinct from the esters of the lower fatty acids, and is largely employed in perfuming soaps, and in compounding artificial otto of rose. It can be prepared by heating geraniol with butyryl chloride in the presence of anhydrous pyridine, and is an oil boiling at 142° to 143° at 13 mm. pressure.  [c.169]

Fit a reflux condenser into the short neck of a 100 or 125 ml. Claisen flask, a separatory funnel into the long neck, and plug the side arm with a small cork (compare Fig. Ill, 31, 1). Place 37 -5 g. (22-5 ml.) of redistilled thionyl chloride in the flask and 22 g. (23 ml.) of n-butyric acid in the separatory funnel. Heat the flask gently on a water bath, and add the -butyric acid during the course of 30-40 minutes absorb the hydrogen chloride evolved in water using the device shown in Fig. 11,13, 8 (compare Fig. 11, 8, 1). When all the acid has been introduced, heat on a water bath for 30 minutes. Rearrange the apparatus and distil collect the crude acid chloride boiling between 70 and 110° in a distilling flask. Finally, redistil from a small Claisen flask with fractionating side arm (Fig. 11,24, 2-5) or from a flask provided with a short fractionating column (e.g., an 11-glass Dufton column. Fig. 11, 15, 2) collect the n-butyryl chlo e at 100-101°. The yield is 23 g.  [c.368]


See pages that mention the term Butyryl chloride : [c.367]    [c.368]    [c.726]    [c.90]    [c.202]    [c.204]    [c.61]    [c.62]    [c.120]    [c.290]    [c.581]   
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Textbook on organic chemistry  -> Butyryl chloride