Ammonium, benzyltriethyl-, chloride

Cyclopropyl sulfones were shown to be obtained either by cyclization of y-p-tosyloxy sulfones 232 with base or by treatment of phenylsulfonylacetonitrile 233a or ethyl phenyl sulfonyl acetate 233b with 1,2-dibromoethane in the presence of benzyltriethyl-ammonium chloride (BTEA) and alkali in good yields. Chang and Pinnick synthesized various cyclopropane derivatives 234 upon initial treatment of carbanions derived from cyclopropyl phenyl sulfone with either alkylating agents or a carbonyl compound and subsequent desulfonylation, as shown below. 

Nitroalkanes react with Jt-deficient alkenes, for example, p-nitro ketones are produced from a,P-unsaturated ketones [41], whereas allylic nitro compounds have been prepared via the Michael-type addition of nitroalkanes with electron-deficient alkynes (Table 6.19). The reaction in either dimethylsulphoxide [42] or dimethyl-formamide [43] is catalysed by potassium fluoride in the presence of benzyltriethyl-ammonium chloride the reaction with dimethyl acetylenedicarboxylate is only successful in dimethylsulphoxide [42], Primary nitroalkanes produce double Michael adducts [42,44], A-Protected a-aminoacetonitriles react with alkynes under catalysed solidiliquid conditions to produce the Michael adducts [45] which, upon treatment with aqueous copper(Il) sulphate, are converted into a,p-unsaturated ketones. 

In one of the earliest studies of phase-transfer catalysed reactions, Makosza and his research group generated dichlorocarbene using a catalytic amount of benzyltriethyl-ammonium chloride in an aqueous sodium hydroxiderchloroform two-phase system [2, 3] and it has become the standard method for the phase-transfer catalytic production of dichlorocarbene and related dihalocarbenes. 

Methylindene undergoes rapid rearrangement to 3-methylindene [13] via the conjugate base, when treated with aqueous sodium hydroxide and benzyltriethyl-ammonium chloride under reaction conditions similar to those described in 9.4.1. 

Anionicallv Activated Alumina. At this time we had also developed an interest in anionically activated alumina. These basic reagents were active in promoting alkylation(42), condensation(43) and hydrolysis(44) reactions. Thus, we impregnated alumina with sodium hydroxide and used this combination both with and without a phase transfer catalyst (benzyltriethyl ammonium chloride). When BTEAC was added, the conversion to ether was decreased and the formation of ester was noted. In the absence of a phase transfer catalyst, the ether became a minor product and methyl phenylacetate became the major product with coproduction of phenylacetic acid. This ester does not result from esterification of the acid as simple stirring of phenylacetic acid with Na0H/A1203 in methanol does not produce methyl phenylacetate. 

B. (+)-trans- -( Pketiyleulfnnyl) -3-phenylexaairidine. A 5-L, three-necked flask is equipped with a mechanical stirrer and a 500-mL pressure-equalizing addition funnel. Into the flask are placed 500 mL of saturated aqueous sodium bicarbonate solution, 12.5 g (0.055 mol) of benzyltriethyl -ammonium chloride (BTEAC) and 122.5 g (0.50 mol) of N-benzylidenebenzene-sulfonamide dissolved in 380 mL of chloroform (Note 7). The reaction mixture is stirred vigorously at 0-5°C in an ice bath while a solution of 111.6 g (0.55 mol) of 85% m-chloroperoxybenzoic acid (MCPBA) dissolved in 1000 mL of chloroform is added dropwise. After the addition of the peracid, which takes about 1 hr, the reaction mixture is stirred for an additional hour at this temperature. A 3-L separatory funnel is used to separate the chloroform... 

Methylpentynol Bulk TLC extracted 50% EtOH (15 ml) RT, 30 min, centrifuged, filtered. ISTD-benzyltriethyl-ammonium chloride cm 75 ID, 28 kV Silica 0.005M barium hydroxide (pH 10) CHCI3-acctonc (4 1) KMnO, methylpseudo-ephedrine 5 min, pseudoephedrine 6.2 min, ephedrine 6.8 min, methylephedrine 7.8 min. norpseudoephedrine 8.1 min, norephedrine 8.8 min GC 2] [1]... 

RCOOH —> RCOOOH.2 This oxidant converts water-insoluble carboxylic acids to the peracid in ether or CH2C12 under the influence of benzyltriethyl ammonium chloride or polyethylene glycol (PEG-400). 

Since dimethyl sulfate decomposes rapidly in concentrated alkaline medium, addition of the powdered tartaric acid amide must begin immediately after the dimethyl sulfate is introduced. The amide should be added as fast as possible (ca. 20-30 min) within the limits of the capacity of the reflux condenser and the mechanical stirrer. The amount of dimethyl sulfate can be increased up to 2.5 equivalents and fresh benzyltriethyl-ammonium chloride can be added toward the end of the addition. With less rapid addition and stirring, the yield drops to 45-55%. 

Glycidk nitrUes. " Glycidic nitriles can be obtained in good yield by the reaction of ketones with chloroacelonitrile in aqueous sodium hydroxide with benzyltriethyl-ammonium chloride as catalyst. 

Figure 3.1 Antimony pentachloride-benzyltriethyl ammonium chloride complex.

The antimony pentachloride-benzyltriethyl ammonium chloride complex (SbCls-TEBA, Figure 3.1), shows quite interesting catalytic efficiency in the acylation of activated aromatic compounds (i.e., toluene, xylenes, aryl ethers) with aromatic and chloroacetyl chlorides. Reactions are carried out with SbCls-TEBA (5% mol) in boiling nitromethane, giving ketones in 73%-96% yield. The catalyst has many advantages, such as ready access, minimal toxicity, reusability, insensitivity to atmosphere and moisture. 

AI3-14906 Ammonium, benzyltriethyl-, chloride Benzenemethanaminium, N,N,N-triethyl-, chloride Benzyl triethyl ammonium chloride Benzyltriethyl-ammonium chloride BTEAC EINECS 200-270-1 Sumquat 2355 TEAC TEBA TEBAC Triethyl-benzylammonium chloride N,N,N-Triethylbenzene-methanaminium chloride. Quaternary ammonium salt solvent for cellulose gelling Inhibitor in polyester resins intermediate In chemical manufxturing. Also used as a fibre dyeing auxilliary and phase transfer catalyst. Solid mp = 185° soluble in H2O (170 g/100 ml). Hexcel Janssen Chimica Zeeland Chem. Inc. 

Phase-transfer catalysis. A Polish group reported that the Wittig-Horner reaction with a-phosphoryl sulfoxides, sulfones, and sulfides could be conducted in a two-phase system (aqueous NaOH-methylene chloride) with benzyltriethyl-ammonium chloride as catalyst. Later work showed that a catalyst was not necessary because these sulfur compounds themselves can function as catalysts for phase-transfer reactions. Thus (1) is an effective catalyst for alkylation of ketones by alkyl halides in the presence of 50% aqueous NaOH. Related, but somewhat less active, catalysts are sulfones such as (2), a-disulfoxides (3), and bisphosphonates (4). 

Alkylation of tosylmethylisocyanide. Tosylmethylisocyanide (4, 514-516 5, 684-685) can be monoalkylated in high yield (75-95%) by primary alkyl halides (including alkyl chlorides and benzyl bromide) under phase-transfer conditions with either this quaternary salt or the less reactive benzyltriethyl-ammonium chloride. Yields are lower with secondary alkyl halides. With more reactive alkyl hahdes, the reaction is conducted at 0° to avoid dialkylation. 

Phosphorylation of primary alcohols and phenols. Zwierzak has found that the Atherton-Todd phosphorylation can be carried out advantageously under phase-transfer eatalysis. Carbon tetrachloride and 50% aqueous sodium hydroxide serve as the solvent pair tetra-/i-butylammonium bromide or benzyltriethyl-ammonium chloride serve equally well as catalysts. Yields are 35 90% for primary alcohols and phenols low yields are obtained from other alcohols. 

A mixture of 1-adamantyl alcohol, aq. 50%-NaOH-soln., and a little benzyltriethyl-ammonium chloride emulsified at 40° by vigorous stirring, chloroform added drop-wise during 2 hrs., and stirring continued 2 hrs. 1-adamantyl chloride. Y ... 

Sodium hydroxide benzyltriethyl-ammonium chloride C-Alkylation in aq. medium... 

See Lauralkonium bromide Ammonium, benzylhexadecyidimethyl-, chloride. See Cetalkonium chloride Ammonium, benzyltriethyl-, chloride. See Benzyltriethyl ammonium chloride Ammonium, benzyltrimethyl-, hydroxide. See Benzyl trimethyl ammonium hydroxide Ammonium biborate CAS 12007-58-8 12228-87-4 (tetrahydrate)... 

Uses Phase transfer catalyst chemical reagent Manuf./Distrib. Acros Org. http //www.acros.be] Amyl http //www.amyi.com] Lancaster Synthesis TCI Am. http //www.tciamerica.com] Yancheng Huaue Pharm. Chem. http //www.huayepharm. com Yixing Fangqiao East Chemical http //www. eastchemicais. com Benzyltriethyl ammonium chloride CAS 56-37-1 EINECS/ELINCS 200-270-1 Synonyms Ammonium, benzyltriethyl-, chloride Benzenemethanaminium, N,N,N-triethyl-, chloride BETEC BTEAC TEBAC N,N,N-Triethylbenzenemethanaminium chloride Triethyl benzyl ammonium chloride Classification Quaternary ammonium salt Empirical C13H22N Cl Formula C6H5CH2N(CI)(C2H5)3 Properties Solid m.w. 227.8 m.p. 197-199 C (dec.)... 

BETEC. See Benzyltriethyl ammonium chloride Betratrim Brand Quaker Oatrim. See Hydrolyzed oat flour Betula. See Methyl salicylate Betula alba. See Birch (Betula alba) leaf extract Birch (Betula alba) sap Birch (Betula alba) extract Birch (Betula alba) oil Betula alba extract. See Birch (Betula alba) extract... 

BTC 8358. See Benzaikonium chloride BTDA BTDA. See 3,3, 4,4 -Benzophenone tetracarboxylic dianhydride BTEAC. See Benzyltriethyl ammonium chloride BTHC. See Butyroyl trihexyl citrate BTMAC BTMAC. See Benzyl trimethyl. ammonium chloride... 

TEA-undecylenoyl hydrolyzed animal protein. See TEA-undecenoyl hydrolyzed collagen TEB. See Triethylborane 1,1,3-Triethoxybutane TEBAC TEBAC. See Benzyltriethyl ammonium chloride... 

N,N,N-Triethylbenzenemethanaminium chloride Triethyl benzyl ammonium chloride. See Benzyltriethyl ammonium chloride Triethylborane... 

Benzyltriethyl ammonium chloride Benzyltrimonium hydrolyzed collagen Betaine Bishydroxyethyl dihydroxypropyl stearaminium chloride Calcium D-pantothenate Calcium DL-pantothenate C12-16 alcohols... 

Acetamide Alkyl trimethyl ammonium chloride Ammonium caprylate Benomyl Benzimidazole carbamate 1,2-Benzisothiazolin-3-one Benzyltriethyl ammonium chloride Chlorine dioxide p-Chloro-m-cresol Chlorophene Cocodiamine acetate Dialkyl methyl benzyl ammonium chloride DIchlorobenzyl alcohol DImethoxytetrahydrofuran DM DM hydantoin Glyoxal Hexachlorophene Hydrogenated tallowtrlmonlum methosulfate N,N -Methylene bismorphollne 2-Methyl-4,5-trlmethylene-4-lsothlazolln-3-one Quaternlum-18 methosulfate Thiophanate Tributyl phosphine Tributyl (tetradecyl) phosphonlum chloride Trioctyl (octadecyl) phosphonlum Iodide VInylene bisthlocyanate biocide mfg. 

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