Dodecyl methyl

CH3(CH2)ioCH2SCH3 + CH3I Dodecyl methyl sulfide Methyl iodide... 

Sodium ionophore VI bis[(12-crown-4)methyl]dodecyl methyl malonate [80403-59-4] M 662.9. Purified by gel permeation or column chromatography. [Preparation and NMR data J Electroanal Chem 132 99 1982.]... 

Notes Mild oxidizing agent (See DMSO Oxidations in Aldehyde Syntheses). A source of the S-Me electrophile. For an odorless protocol 1 Instead of DMSO, dodecyl methyl sulfide is used in the reaction thus, eliminating the dimethylsulfide by-product. 

As shown in the text, dodecyldimethylsulfonium iodide may be prepared by reaction of dodecyl methyl sulfide with methyl iodide. An alternative method is the reaction of dodecyl iodide with dimethyl sulfide. 

HjC R Te2 f NaBH4/C H5OH H25C12-13r dodecyl methyl tellurium 83 99 0.04 - 3... 

Dodecyl phenyl tellurium dioxide was converted by 3-chloroperoxybenzoic acid in methanol to dodecyl methyl ether in 87% yield2. 

Because of the foul smell of DMS, several odourless versions of Corey-Kim and Swern oxidations have been reported. For example, odourless dodecyl methyl sulfide (Dod-S-Me) is an alternative to DMS in Corey-Kim oxidations. 

Similarly, when dodecyl methyl sulfoxide (C12H25SOCH3) is used in the Swern oxidation, the odourless Dod-S-Me by-product instead of foul-smelling DMS is formed. 

This Dod-S-Me recovered from the reaction can be reoxidized to dodecyl methyl sulfoxide by sodium periodate. 

Cationic surfactants can also be modified by incorporating PEO chains, for example dodecyl methyl polyethylene oxide ammonium chloride having the structure ... 

Sodium ionophore VI his[(12-crown-4)methyl]dodecyl methyl malonate [80403-59-4] M... 

Bowers and Thompson (1963), after having established that the completely saturated hexahydrofamesol (17) is also effective, investigated several saturated, nonbranched alcohols and their methyl ethers. Of these, dodecanol and dodecyl methyl ether (18) were active. Similar results were reported by Schneiderman et al. (1965), who found that molecular dimensions play a decisive role in the exertion of the action. 

The other variation utilizes readily obtainable, inexpensive, and odorless dodecyl methyl sulfide (16) to afford oxidized products in excellent yields.4 For example, after adding testosterone (15) to a stirring solution of NCS and 16 at -40 °C, the desired ketone 17 was obtained in 97% yield after TEA addition. 

An unavoidable by-product of the Swem reaction is the volatile dimethylsulphide which, on account of its unpleasant smell, is a reagent regulated by offensive odour control laws. This makes large scale chemistry problematic, especially in industry. To overcome this, several methods exist to perform the Swem oxidation under odourless conditions. For example, Node et al. outline a protocol for the Swem oxidation which uses dodecyl methyl sulfoxide in place of methyl sulfoxide,12 while Crich and co-workers have developed a fluorous Swem oxidation reaction that uses tridecafluorooctylmethyl sulfoxide 17,l3a,b This reagent can be recovered via a continuous fluorous extraction procedure and recycled by reoxidation with hydrogen peroxide. Additionally, the fluorous DMSO is crystalline, odourless and soluble in CH2CI2 to —45 °C. 

Beilstein Handbook Reference) AI3-00669 BRN 1767780 Dodecanoic acid, methyl ester EINECS 203-911-3 FEMA number 2715 HSDB 5550 Laurie acid, methyl ester Metholene 2296 Methyl dodecanoate Methyl dodecylate Methyl laurate Methyl laurinate Methyl n-dodecanoate NSC 5027 Stepan C40 Uniphat A40. Used as an intermediate in the manufacture of detergents, emulsifiers, wetting agent, stabilizers, lubricants, plasticizers, texfiles, flavoring. Liquid mp = 5.2° bp n 267 d =... 

One drawback of these reactions is the formation of volatile, odorous dimethyl sulfide. Various solutions to this problem have been reported, such as the use of dodecyl methyl sulfoxide (Ci2H25SOMe) with oxalyl chloride followed by triethy-lamine. The by-product dodecyl methyl sulfide is non-volatile and yields are only slightly reduced in comparison with the use of dimethyl sulfoxide. 

---