- Facile synthesis of α-iodo carbonyl compounds and α-iodo dimethyl ketals using molecular iodine and trimethylorthoformate
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A novel and direct method for the synthesis of α-iodo ketones and α-iodo dimethyl ketals from acetophenones using iodine and trimethylorthoformate under neutral conditions is described herein.
- Yadav,Kondaji,Shiva Ram Reddy,Srihari
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p. 3810 - 3813
(2008/09/21)
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- SYNTHESIS OF 4,4-DISUBSTITUTED CYCLOHEXENONES. PART 1. BAEYER-VILLIGER FRAGMENTATION OF 1-METHOXYBICYCLOOCT-5-ENONES.
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The sodium acetate-buffered peracetic acid oxidation of various 1-methoxybicyclooct-5-enones (4a-f), and (14), prepared by hydrolysis of the adducts (3) derived from dihydroanisole derivatives (2) and 2-chloroacrylonitrile leads to 4-
- Holmes, Andrew B.,Madge, Nigel C.
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p. 789 - 802
(2007/10/02)
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- Electrophilic Chlorination of 4-Methylphenols with Molecular Chlorine. Synthesis of Dimethoxy Aromatics by Methanolysis of 4-Chloro-4-methylcyclcohexa-2,5-dienones
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The chlorination of p-cresol (1a), 2,4-dimethylphenol (1b), 3,4-dimethylphenol (1c), 2,4,5-trimethylphenol (1d), 2,4,6-trimethylphenol (1e) and the various possible mono- and dichloro derivatives of these phenols (3a-d, 6a and 6 c) with molecular chlorine was investigated in dichloromethane or dimethyl formamide solution.The 2,6-substituted p-cresol derivatives all give quantitative yields of 4-chloro-4-methylcyclohexa-2,5-dienones (5b, 5d, 7a, 7c and 2e), whereas the less substituted p-cresol derivatives give a 20-25percent yield of corresponding 4-chloro-4-methylcyclohexa-2,5-dienones (2a-d, 5a and 5c), the other products being chlorinated phenols.Treatment of 4-chloro-4-methylcyclohexa-2,5-dienones with at least one of the double bonds of the ring unsubstituted (2a-c and 4a) with methanol gave a quantitative yield of a 1,3-dimethoxybenzene derivative (9a-c and 10), whereas similar treatment of 4-chloro-2,4,5-trimethylcyclohexa-2,5-dienone (2d) gave 5-methoxy-2,3-dimethylbenzyl methyl ether (11).Treatment of the other 4-chlorodienones with methanol gave the corresponding 4-methoxydienones.Electrophilic chlorination of certain p-cresol derivatives followed by methanolysis hence is a facile although low-yield method for 3-methoxylation or selective side chain oxidation of these p-cresol derivatives.
- Bergquist, Karl-Erik,Nilsson, Anders,Ronlan, Alvin
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p. 675 - 684
(2007/10/02)
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