- METHOD OF CONVERTING ALCOHOL TO HALIDE
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The present invention relates to a method of converting an alcohol into a corresponding halide. This method comprises reacting the alcohol with an optionally substituted aromatic carboxylic acid halide in presence of an N-substituted formamide to replace a hydroxyl group of the alcohol by a halogen atom. The present invention also relates to a method of converting an alcohol into a corresponding substitution product. The second method comprises: (a) performing the method of the invention of converting an alcohol into the corresponding halide; and (b) reacting the corresponding halide with a nucleophile to convert the halide into the nucleophilic substitution product.
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Page/Page column 51; 132; 138
(2017/01/02)
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- Chlorination of aliphatic primary alcohols via triphosgene-triethylamine activation
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Activation of primary aliphatic alcohols with triphosgene and triethylamine mixtures afforded either alkyl chloride or diethylcarbamate products, and the switch in selectivity appeared to be driven by sterics. The reaction conditions to achieve this highly useful transformation were unexceptionally mild and readily tolerated by a wide range of sensitive functionalities.
- Ayala, Caitlan E.,Villalpando, Andres,Nguyen, Alex L.,McCandless, Gregory T.,Kartika, Rendy
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supporting information; experimental part
p. 3676 - 3679
(2012/09/08)
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- A Convenient access to (All-rac)-α-tocopherol acetate from linalool and dihydromyrcene
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Refluxing trimethylhydroquinone 2 in 10:1 dodecane/CH2Cl 2 with linalool 3b (two-fold excess) and camphorsulfonic acid, then treating the crude condensation product (consisting of a mixture of the chromanols 1b and 1c, alongside the tricyclic compounds 9 and 10) sequentially with Ac2O and m-CPBA afforded, after removal by column chromatography of the 9/10 acetates, a mixture of the regioisomeric epoxides 1jOAc and 1kOAc (ratio 9:1, total 60%). Treatment of this mixture with Al(O-i-Pr)3 followed by CuI-catalysed Wurtz coupling of the acetates of the resulting allylic alcohols with citronellylmagnesium chloride 12a, and finally hydrogenation then provided the title acetate (overall 46% from 2).
- Gembus, Vincent,Sala-Jung, Nathalie,Uguen, Daniel
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experimental part
p. 829 - 842
(2009/12/25)
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- ISONITRILES AND ANTIFOULING AGENTS AGAINST THE ADHESION OF AQUATICS
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Isonitriles represented by the general formula (1) and antifouling agents against the adhesion of aquatics containing the same: (1) wherein R1 is CH2X (wherein X is hydroxy, halogeno, isocyano, amino, substituted amino, or optionally substituted, alkoxy, alkenyloxy, acyloxy, organosulfonyloxy, organosulfenyl, organosulfinyl, organosulfonyl, amido, or imido) or COOR4 (wherein R4 is optionally substituted, alkyl, alkenyl, or aralkyl); and R2 and R3 are each independently alkyl.
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Page/Page column 19-20
(2010/10/20)
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- A CONVENIENT METHOD FOR THE TRANSFORMATION OF ALCOHOLS TO ALKYL CHLORIDES USING N,N-DIPHENYLCHLOROPHENYLMETHYLENIMINIUM CHLORIDE
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N,N-Diphenylchlorophenylmethyleniminium chloride reacts smoothly with a variety of alcohols in the presence of triethylamine to afford the corresponding alkyl chlorides in high yields.Replacement of a hydroxyl group at an asymmetric carbon atom with chloride proceeds with complete inversion.
- Fujisawa, Tamotsu,Iida, Sachio,,Sato, Toshio
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p. 1173 - 1174
(2007/10/02)
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