Tricaprylmethylammonium chloride

To promote phase transfer in the toluene/H20 solvent system, 1 drop of Aliquat 336 (tricaprylmethylammonium chloride, Aldrich) was added. For kinetic studies, aliquots (0.1 ruL) were withdrawn by syringe at timed intervals (20-360 s)... 

The solvents and coupling reagents were reagent grade materials. The tricaprylmethylammonium chloride (Adogen 464) was not purified further. Intrinsic viscosities were measured in chloroform at 25. Infrared spectra for hydroxyl analysis were measured on 2.5% solutions in carbon disulfide (vs. carbon disulfide2.in a cell with a 1.00 cm path length. The absorbance at 3610 cm was subtracted from a similar spectrum of 2 which had been quantitatively acetylated. 

A number of different ionic liquids have been screened in the ruthenium-catalysed oxidation of secondary alcohols (see Scheme 5.18). Three different ruthenium compounds, RuC13, RuCl2(PPh3)3 and [RuCFl/i-cymene) were compared and best results were obtained with RuCl2(PPh3)3.[76] While imidazolium-based ionic liquids gave only poor results (anion = Cl) or suppressed the reaction completely (anion = [BF4] or [PF6] ), tetraalkylammonium-based solvents such as Aliquat 336 (tricaprylmethylammonium chloride) or tetramethylammonium hydroxide afforded much better yields. 

SYNS ALIQUAT336 AIJQUAT336N ALIQUAT 336-PTC N-METHYL-N,N-DIOCTYL-l-OCTAN-AiMINIUM CHLORIDE METHYLTRICAPRYLYL-AMMONIUM CHLORIDE 1-OCTANAMINIUM, N-METHYDN.N-DIOCTYL-, CHLORIDE (9CI) TRICAPRYLMETHYLAMMONIUM CHLORIDE TRICAPRYLYLMETHYLAMMONIUM CHLORIDE TRIOCTYLMETHYLAMMONIUM CHLORIDE... 

Caution Tricaprylmethylammonium chloride (Aliquat 336) is a toxic irritant. Handle with care. 

Into a 50-mL round-bottomed flask weigh 0.8 g of tricaprylmethylammonium chloride, 8.00 g of diethyl malonate, 7.53 g of 1-bromobutane, and 8.3 g of anhydrous potassium carbonate. Attach a water-cooled reflux condenser and reflux the reaction mixture for 1.5 h (Fig. 1). Allow the... 

Two unusual approaches to TLC of amoxicillin and other penicillins are the use of silica gel impregnated with tricaprylmethylammonium chloride with a methanol/water mobile phase [111], and the use of micellar solutions as mobile phase [112]. The latter was reported to give better separation of penicillins and their degradation products than organic mobile phases. 

Aliquat = tricaprylmethylammonium chloride [MeN(C8Hn)3Cl] p-An = para-anisyl [4-MeOC6H4] aq. = aqueous atm = atmosphere... 

ChHi60, Mr 164.25, bpi kPa 78-79 °C, tfi° 0.9423, n 1.4989 occurs in jasmine absolute and contributes to its typical jasmine odor. It is a pale yellow, viscous liquid with a strong jasmine odor. Various stereospecific syntheses for c/s-jasmone have been reported. A patented method involves alkylation of 3-methyl-2-cyclopen-ten-l-one with cz. y-2-pentenyl chloride in an alkaline medium in the presence of a phase-transfer catalyst (e.g., tricaprylmethylammonium chloride) [121] ... 

A more cost-effective and reliable route to 464 uses lactamides 465 or 467 as the precursor [95,117] (Scheme 67). These are readily available from lactamides 6c and 466 by standard inexpensive benzylation conditions (benzyl chloride, sodium hydride) or phase-transfer conditions (benzyl chloride, sodium hydroxide, tricaprylmethylammonium chloride, 92% yield). These alkylations, which have also been performed with / -chlorobenzyl chloride and / -methoxybenzyl chloride, proceed with no racemization. Reduction of lactamides 465 or 467 with sodium bis(2-methoxyethoxy)aluminum hydride (Vitride) furnishes (/S)-2-benzyl-oxypropanal (464) in high yield. The aldehyde itself is not very stable, and has a propensity to hydrate, so it should be used immediately after preparation. 

Quaternary onium salts. Quaternary ammonium salts include trioctymethylammo-nium chloride (Starks catalyst), Aliquat 336, tricaprylmethylammonium chloride, tetrabutylammo-nium hydrogen sulfate (Brandstrom s catalyst), and benzyltrimethylam-monium chloride (Mqkosza s catalyst) quaternary ammonium salts can also be generated in situ from trialkylamines, etc. Other quaternary onium salts include tetrabutylphospho-nium bromide, tetraphenylphosphonium bromide, triphenylbenzylphosphonium chloride, tetraphenylarsonium chloride, and triphenylsulfonium chloride, etc. Special quaternary salts are 4-aminopyridinium salts, bis-(quaternary ammonium) [R3N -(CH2) -NR3" R3N -(CH2) -0-(CH2) -NRj ] salts, 4,4 -dialkylbipyridinium salts, cluster quaternary ammonium [e.g., P(C6H4S03"NR4)3] salts, crown-quaternary salts [e.g. (18-crown-6)-(CH2)9PBuj Br ], and chiral V-(4-trifluoromethyl)benzylcinchonium bromide, etc. 

Reagents and Equipment. Weigh and place 106 mg (0.51 mmol) of 9-anthraldehyde in a 10-mL round-bottom flask containing a magnetic stirrer. Add 2 drops of AHquat 336 (tricaprylmethylammonium chloride), 120 gL (0.58 mmol)... 

Szilagyi, J., Kovacs-Hadady, K., and Kovacs, A. (1993). OPLC study of retention of aromatic N glycosides on layers impregnated with tricaprylmethylammonium chloride. J. Planar Chromatogr.—Mod. TLC 6 212-215. 

Quaternary alkylammonium salts, tertiary amines, and crown ethers have all been utilized as catalysts in the reaction of hydroxide with chloroform to yield dichlorocarbene. The most commonly utilized catalyst has been benzyltriethylammonium chloride (see Sect. 1.7) but other quaternary ammonium chloride catalysts have proved effective. Cetyltrimethylammonium chloride and tricaprylmethylammonium chloride (Aliquat 336) have both been used effectively in the cyclopropanation of simple alkenes. The use of Z e a-hydroxyethyltrialkylammonium hydroxides as phase transfer catalysts results in increased regioselectivity in the addition of dichlorocarbene to olefins [12]. Crown ethers such as dibenzo and dicyclohexyl-18-crown-6 have both been utilized in place of quaternary ammonium compounds. 18-Crown-6 has also been used as a catalyst in the phase transfer thermal decomposition of sodium trichloroacetate to yield dichlorocarbene [13]. 

Dicyclopropylvinylidene has been generated by treatment of 2-(N-nitrosoacetylamino)-1,1-dicyclopropylethanol with 50% NaOH in the presence of a catalytic amount of tricaprylmethylammonium chloride (TCMAC) and trapped in situ by cyclohexene... 

Allylic ethers of aldehyde cyanohydrins have also been prepared under phase transfer conditions [23]. The organic phase, consisting of aldehyde cyanohydrin, an allylic halide (preferably the bromide) and dichloromethane is brought into contact with aqueous sodium hydroxide and tricaprylmethylammonium chloride. Anion exchange in the aqueous phase leads to the tricaprylmethylammonium/hydroxide ion pair, which reacts with the cyanohydrin to form the corresponding alkoxide. Reaction of the alkoxide with the allylic halide leads to the allylic ether of the cyanohydrin (Eq. 7.9). The formation of small amounts of allylic nitriles is apparently due to the side... 

In recent years, the quaternary ammonium-functionalized ILs have been investigated widely because of its cheap, low toxicity properties. A kind of ILs was designed and synthesized by tricaprylmethylammonium chloride (Aliquat 336 or A336) and traditional carboxylic acid and phosphoric acid extractant [2]. Because the cation and anion of this kind of ILs are all the functional group for the REEs extraction, we called them bifunctional ionic liquid extractants (Bif-ILEs). Bif-ILEs could be synthesized by acid/base neutralization, and this reaction process was under mild condition, with easier purification and good yield (about 70-80 %). 

HDC reaction was performed in gas phase or under multiphase conditions. Multiphase reaction conditions were following 50°C, substrate solution in iso-octane, Aliquat 336 (tricaprylmethylammonium chloride, Aldrich), KOH (5% aqueous solution), catalyst, hydrogen flow 5 ml/min, nonane as the internal standard. Samples were taken from organic phase during the reaction at fixed intervals and analyzed by GC. 

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