2-isopropyl- -acetic acid chloride

Another important derivative of m-cresol used in the manufacture of plant protection agents is m-phenoxytoluene, which can be produced from m-cresol and chloro- or bromobenzene at temperatures of 200 °C, with copper catalysts. m-Phenoxytoluene is converted into m-phenoxybenzoic acid methyl ester by oxidation with a cobalt acetate/KBr catalyst and subsequent esterification m-phenoxybenzoic add methyl ester serves as an intermediate in the production of m-phenoxybenzaldehyde, which is used as the raw material in the production of the synthetic pyrethroid insecticide, fenvalerate (see Chapter 6.3.2). The cyanohydrin is formed in-situ, then made to react with 2-isopropyl-(4-chlorophenyl) acetic acid chloride to yield fenvalerate, which was developed by Sumitomo Chemical in 1972. Pyrethroid insecticides are distinguished by their low toxicity and high activity. 

PMMA is not affected by most inorganic solutions, mineral oils, animal oils, low concentrations of alcohols paraffins, olefins, amines, alkyl monohahdes and ahphatic hydrocarbons and higher esters, ie, >10 carbon atoms. However, PMMA is attacked by lower esters, eg, ethyl acetate, isopropyl acetate aromatic hydrocarbons, eg, benzene, toluene, xylene phenols, eg, cresol, carboHc acid aryl hahdes, eg, chlorobenzene, bromobenzene ahphatic acids, eg, butyric acid, acetic acid alkyl polyhaHdes, eg, ethylene dichloride, methylene chloride high concentrations of alcohols, eg, methanol, ethanol 2-propanol and high concentrations of alkahes and oxidizing agents. 

This reaction mixture is kept between 0°C and -i-5°C for six hours, with agitation and under an inert atmosphere, then 5 cc of a 0.2N solution of acetic acid in toluene are added. The mixture is extracted with toluene, and the extracts are washed with water and evaporated to dryness. The residue is taken up in ethyl acetate, and then the solution Is evaporated to dryness in vacuo, yielding a resin which is dissolved in methylene chloride, and the solution passed through a column of 40 g of magnesium silicate. Elution is carried out first with methylene chloride, then with methylene chloride containing 0.5% of acetone, and 0.361 g Is thus recovered of a crude product, which is dissolved in 1.5 cc of isopropyl ether then hot methanol Is added and the mixture left at 0°C for one night. 

ETHYLENE GLYCOL ETHYL MERCAPTAN DIMETHYL SULPHIDE ETHYL AMINE DIMETHYL AMIDE MONOETHANOLAMINE ETHYLENEDIAMINE ACRYLONITRILE PROPADIENE METHYL ACETYLENE ACROLEIN ACRYLIC ACID VINYL FORMATE ALLYL CHLORIDE 1 2 3-TRICHLOROPROPANE PROPIONITRILE CYCLOPROPANE PROPYLENE 1 2-DICHLOROPROPANE ACETONE ALLYL ALCOHOL PROPIONALDEHYDE PROPYLENE OXIDE VINYL METHYL ETHER PROPIONIC ACID ETHYL FORMATE METHYL ACETATE PROPYL CHLORIDE ISOPROPYL CHLORIDE PROPANE... 

Acetamido-4-amino-6-chloro-s-triazine, see Atrazine Acetanilide, see Aniline, Chlorobenzene, Vinclozolin Acetic acid, see Acenaphthene, Acetaldehyde, Acetic anhydride. Acetone, Acetonitrile, Acrolein, Acrylonitrile, Aldicarb. Amyl acetate, sec-Amyl acetate, Bis(2-ethylhexyl) phthalate. Butyl acetate, sec-Butyl acetate, ferf-Butyl acetate, 2-Chlorophenol, Diazinon. 2,4-Dimethylphenol, 2,4-Dinitrophenol, 2,4-Dinitrotoluene, 1,4-Dioxane, 1,2-Diphenylhydrazine, Esfenvalerate. Ethyl acetate, Flucvthrinate. Formic acid, sec-Hexyl acetate. Isopropyl acetate, Isoamyl acetate. Isobutyl acetate, Methanol. Methyl acetate. 2-Methvl-2-butene. Methyl ferf-butvl ether. Methyl cellosolve acetate. 2-Methvlphenol. Methomvl. 4-Nitrophenol, Pentachlorophenol, Phenol. Propyl acetate. 1,1,1-Trichloroethane, Vinyl acetate. Vinyl chloride Acetoacetic acid, see Mevinphos Acetone, see Acrolein. Acrylonitrile. Atrazine. Butane. 

The purpose of the wash with diethyl ether and isopropyl alcohol is to remove the remaining acetic acid and any residual hydrogen chloride, which may cause decomposition during the subsequent crystallization. 

Isopropyl-2-phenylcyclobutanol (29) was obtained by hydroboration-oxidation of 4-iso-propyl-l-phenylcyclobutene.38 In a synthetically useful procedure, hydrolysis of 1,2-bis(phenylsulfanyl)cyclobutene at room temperature in a solution of copper(IT) chloride and titanium(IV) chloride in acetic acid gave 2-(phenylsulfanyl)cyclobutanone (30) in 85% yield.39... 

Figure 2. Rejection performance of five different RO membranes (6). A, methanol B, aniline C, formaldehyde D, methyl acetate E, acetic acid F, urea G, ethanol H, acetone 1, hydroquinone J, isopropyl alcohol Kt glycerol L, sodium chloride M, ethyl ether N, phenol. Conditions pressure, 40.8 atm temperature, 24 °C feed, 0.30 gal/min.

Oxidation of 8-hydroxymethyl-2-isopropyl-l 1 //-pyrido[2,l-b]quinazolin-11-one with pyridinium chlorochromate in methylene chloride gave the 8-carboxaldehyde, which was converted into its 8-aminomethyl derivatives by reacting with amines followed by reduction of the Schiff bases with sodium cyanoborohydride in acetic acid (87JOC2469). 

The following route is described in US Patent 4,145,552 At ambient temperature, over a period of thirty minutes, a solution of 33.8g (O.lmol) of (-)-vincadiformine in a mixture of 140 ml of anhydrous dimethylformamide and 140 ml of anhydrous toluene is added to a suspension of 2.64 g (0.11 mol) of sodium hydride in a mixture of 200 ml of anhydrous tetrahydrofuran, 20 ml of anhydrous hexamethylphosphotriamide (EMPT) and 18.7 ml (0.14 mol) of trimethyl phosphite. When the release of hydrogen has finished (about two hours later), the solution is cooled to -10°C and then stirred under an oxygen atmosphere until absorption ceases (duration 3 hours). Still at -10°C, 136 ml of glacial acetic acid are added, and the mixture is then left at ambient temperature for two hours. After the addition of 500 ml of 1 N sulfuric acid, the aqueous phase is isolated, reextracted with 150 ml of isopropyl ether, made alkaline with 350 ml of 11 N ammonia, then extracted 3 times with 300 ml aliquots of methylene chloride. After drying over calcium... 

Vinylic substitutions in otherwise unreactive systems can take place easily in the presence of metal salts. The chlorine atom of vinyl chloride is replaced by acetic acid, isopropyl alcohol and n-butylamine in the presence of catalytic amounts of PdCl2 in iso-octane (Stern et al., 1966). 

The industrial production of Crixivan (9 H2S04) took advantage of the chirality of (IS,2R)-aminoindanol to set the two central chiral centers of 9 by an efficient diastereoselective alkylation-epoxidation sequence.17 The lithium enolate of 12 reacted with allyl bromide to give 13 in 94% yield and 96 4 diastereoselective ratio. Treatment of a mixture of olefin 13 and V-chlorosuccinimide in isopropyl acetate-aqueous sodium carbonate with an aqueous solution of sodium iodide led to the desired iodohydrin in 92% yield and 97 3 diastereoselectivity. The resulting compound was converted to the epoxide 14 in quantitative yield. Epoxide opening with piperazine 15 in refluxing methanol followed by Boc-removal gave 16 in 94% yield. Finally, treatment of piperazine derivative 16 with 3-picolyl chloride in sulfuric acid afforded Indinavir sulfate in 75% yield from epoxide 14 and 56% yield for the overall process (Scheme 24.1).17-22... 

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