Octanoyl chloride

Many of the perfluoroaLkyl carboxyUc acids were first prepared by the electrochemical fluorination (ECF) of the corresponding carboxyUc acids (7). In ECF acid chlorides are converted to the corresponding perfluoroacid fluorides as shown in equation 1 for octanoyl chloride. 

During electrochemical fluorination retention of important functional groups or atoms in molecules is essential. Acyl fluorides and chlorides, but not carboxylic acids and anhydrides (which decarboxylate), survive perfluorination to the perfluorinated acid fluorides, albeit with some cyclization in longer chain (>C4) species [73]. Electrochemical fluorination of acetyl fluoride produces perfluoro-acetyl fluoride in 36-45% yields [85]. Electrochemical fluorination of octanoyl chloride results in perfluorinated cyclic ethers as well as perfluorinated octanoyl fluonde. Cyclization decreases as initial substrate concentration increases and has been linked to hydrogen-bonded onium polycations [73]. Cyclization is a common phenomenon involving longer (>C4) and branched chains. a-Alkyl-substituted carboxylic acid chlorides, fluorides, and methyl esters produce both the perfluorinated cyclic five- and six-membered ring ethers as well as the perfluorinated acid... 

Poly(hydroxymaleimide-co-hydroxystyrene) (5.60 mmol) was dissolved in 20 ml of /V-mcthylpyrralidonc and then cooled to 0°C. The solution was then treated with tri-ethylamine (20.16 mmol) and stirred for 60 minutes and then further treated with the step 4 product (0.656 g) and octanoyl chloride (4.03 mmol). The mixture was heated to ambient temperature and stirred for 24 hours and then precipitated by pouring in methanol and water. It was filtered, extracted with methanol, and 5.3 g product isolated. 

Other studies by Drakesmith and Hughes [124] have used the fluorination of propene and octanoyl chloride as model compounds to investigate the effects of anode potential, current density, reactant concentration, temperature, etc. on reproducibility, product structure, distribution and yield in novel cell designs ranging in scale from 100 ml to 1001 cell capacities. 

In a later publication [ 129], using the same equipment, Liu et al. describe process improvements in the electrochemical fluorination of octanoyl chloride in which formation of polymeric tar at the anode surface was limited by addition of a mercaptan (1-methyl-1-propanethiol), and by constant current density operation (7 mA cm-2). Continuous operation was achieved by frequent additions of a solution of reactant in hydrogen fluoride. Conversion of reactant to perfluori-nated products was increased to 80%, with good selectivity. 

The possibility of obtaining real improvements in the industrial production of perfluorooctanoic acid by using perfluorohexyl acetyl chloride in place of octanoyl chloride as starting material has been investigated [136]. In particular, the effect of blocking the formation of cyclic ethers on the yield of the perfluoro-acid was examined this was, however, less than expected due to the increased formation of perfluoro- -heptane. 

Scheme 36. Composition of reaction mixtures in the ECF of 4-(perfluoro-n-butyl)-n-butanoyl chloride (Expts.l -4) and n-octanoyl chloride (Expts.5-6)...

Phenyl heptyl ketone has been prepared by the Friedel-Crafts acylation of benzene with octanoyl chloride.6 It is also a product of the thermal decomposition of the mixed ferrous salts of benzoic and octanoic acids.7... 

Benzene Octanoyl chloride 1-Phenyl-1-octanone 1-Phenyloctane... 

Add octanoyl chloride and then the b/ s(4-pivaloxybutyl)zinc solution (4 mL of the above prepared solution). 

A recent article reported the use of strongly acidic mesoporous aluminosilicates prepared from zeolite seeds in the acylation of anisole with octanoyl chloride.[30] The mesoporosity improving the transport of the reactants and the presence of strong acid sites lead to high conversion (>90 %) and high selectivity (100 %). 

CKH,0124-07-2) see Orlistat octanoyl chloride (QH15CIO 111-64-8) see Orlistat octylamine... 

Octanoyl chloride (1.67 mol) was heated to 55 °C, Br2 (2.34 mol) added over 8 hours, and the reaction stirred overnight. Thereafter, the mixture was distilled at 111 °C at 8mmHg, and 100% yield of a mixture of 2-bromooctanoyl chloride and 2-bromooctanoyl bromide, 35 65, isolated. 

OCtanoyl chloride. (capryloyl chloride sometimes called caprylyl chloride). CHjfCFyjCOCl. 

Ioxynil and bromoxynil can be easily esterified with add chlorides ydth longer carbon atom chains. Thus, esterified with octanoyl chloride, ioxynil octanoate and bromoxynil octanoate are formed. These derivatives are readily soluble in xylene (SOO and 400 g/1 resp.), and are thus, suitable for the preparation of emulsifiable concentration formulations (Totril, 250 g ioxynil/1) and Brominal , 240 g active ingredient/1. In the plants the esters are degraded to the parent herbidde and exert their action in this form. 

Acylation of isobutylbenzene with acetic anhydride leads with high yield and selectivity to para-acetylisobutylbenzene (Eq. 9) which is an intermediate in the synthesis of ibuprofen, an important antiinflammatory drug [18]. With H/1 zeolite at 140 °C after 1 h the yield is 80 % with 96 % para selectivity. Acylation of tetra-lin with acid chlorides and different zeolites has also been studied [19], For this reaction again acetyl chloride is much less reactive than higher acid chlorides such as butanoyl or octanoyl chloride. The selectivity is in favor of the 2-substituted isomer (85-90%) and limited quantities of the 1 isomer (10-15%) are formed (Eq. 10). 

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