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P2P [Phenylacetone] Via Aldol & Bayer Villager

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P2P [Phenylacetone] Via Aldol & Bayer Villager C:\Documents and Settings\HP_Administrator.YOUR-4DACD0EA75\My Documents\GHB\Hive Ark\Ark\arch\forum\topic\topic_19.html Synthetikal Archive P2P [Phenylacetone] via aldol & Bayer Villager Name P2P [Phenylacetone] via aldol & Bayer Villager P2P [Phenylacetone] via aldol & Bayer Villager fan of Ok, zwitterion Bio and two dogs posted awhile back, what I think would be one of the most overlooked synthesis of Phenylacetone's An acid catalysed Aldol Condensation, followed by a Bayer-Villager, peracid, eventully gives yield of P2P. The literature is well documented, and verified by many former researchers. MEK+Benzaldehyde--->MethylPhenylButanone I vaguely remember Bio saying that is also could be achieved with Acetone and benzene, respectfully 1) An acid catalysed Aldol condensation of Benzaldehyde and Methyl Ethyl Ketone to give Methyl Phenyl Butenone ie C6H5CHO + CH3CH2COCH3 + dryHCL ---> C6H5CH=C(COCH3)CH3 2) The unsaturated ketone undergoes the Baeyer-Villiger oxidation with peroxy acids to give the enol ester of Phenyl propanone ie C6H5CH=C(COCH3)CH3 + RCO3H ----> C6H5CH=C(OCOCH3)CH3 3) The enol ester is then saponified with 10% NaOH solution to give Phenyl Propanone in about 35% yield based on the unsaturated ketone. &--1050;&--1086;&--1085;&--1076;&--1077;&--1085;&--1089;&--1072;&-- 1094;&--1080;&--1103; Aldol. 200 gms Benzaldehyde &--1080; 300 gms Methyl Ethyl Ketone &--1089;&-- 1084;&--1077;&--1096;&--1080;&--1074;&--1072;&--1102;&--1090;&-- 1089;&--1103; &--1074; &--1083;&--1080;&--1090;&--1088;&--1086;&-- 1074;&--1086;&--1084; &--1093;&--1080;&--1084;&--1080;&--1095;&-- Page 1 - 2009-05-22 22:36:02 C:\Documents and Settings\HP_Administrator.YOUR-4DACD0EA75\My Documents\GHB\Hive Ark\Ark\arch\forum\topic\topic_19.html 1077;&--1089;&--1082;&--1086;&--1084; &--1089;&--1090;&--1072;&-- 1082;&--1072;&--1085;&--1077; &--1080; &--1086;&--1093;&--1083;&-- 1072;&--1078;&--1076;&--1072;&--1102;&--1090;&--1089;&--1103; &-- 1085;&--1080;&--1078;&--1077; 5C.&--1052;&--1077;&--1076;&--1083;&-- 1077;&--1085;&--1085;&--1086; &--1085;&--1072;&--1089;&--1099;&-- 1097;&--1072;&--1077;&--1084; &--1093;&--1083;&--1086;&--1088;&-- 1086;&--1074;&--1086;&--1076;&--1086;&--1088;&--1086;&--1076;&-- 1086;&--1084; &--1087;&--1086;&--1082;&--1072; &--1089;&--1084;&-- 1077;&--1089;&--1100; &--1085;&--1077; &--1091;&--1074;&--1077;&-- 1083;&--1080;&--1095;&--1080;&--1090;&--1089;&--1103; &--1074; &-- 1074;&--1077;&--1089;&--1077; &--1085;&--1072; 40 &--1075;. &--1042;&- -1085;&--1072;&--1095;&--1072;&--1083;&--1077; &--1089;&--1084;&-- 1077;&--1089;&--1100; &--1087;&--1088;&--1086;&--1079;&--1088;&-- 1072;&--1095;&--1085;&--1072;&--1103; &--1087;&--1086;&--1090;&-- 1086;&--1084; &--1085;&--1072;&--1095;&--1080;&--1085;&--1072;&-- 1077;&--1090; &--1082;&--1088;&--1072;&--1089;&--1085;&--1077;&-- 1090;&--1100; &--1080; &--1089;&--1090;&--1072;&--1085;&--1086;&-- 1074;&--1080;&--1090;&--1089;&--1103; &--1084;&--1091;&--1090;&-- 1085;&--1086;&--1081; &--1085;&--1072;&--1089;&--1090;&--1086;&-- 1083;&--1100;&--1082;&--1086; &--1095;&--1090;&--1086; &--1085;&-- 1077;&--1074;&--1080;&--1076;&--1085;&--1086; &--1085;&--1072;&-- 1089;&--1082;&--1074;&--1086;&--1079;&--1100;. &--1057;&--1084;&-- 1077;&--1089;&--1100; &--1074;&--1099;&--1076;&--1077;&--1088;&-- 1078;&--1080;&--1074;&--1072;&--1077;&--1084; &--1085;&--1086;&-- 1095;&--1100; &--1080; &--1086;&--1085;&--1072; &--1089;&--1090;&-- 1072;&--1085;&--1086;&--1074;&--1080;&--1090;&--1089;&--1103; &-- 1082;&--1086;&--1088;&--1080;&--1095;&--1085;&--1077;&--1074;&-- 1086;&--1081;. &--1052;&--1086;&--1077;&--1084; &--1074;&--1086;&-- 1076;&--1086;&--1081; &--1080; &--1079;&--1072;&--1090;&--1077;&-- 1084; 10% &--1088;&--1072;&--1089;&--1090;&--1074;&--1086;&--1088;&- -1086;&--1084; NaOH, &--1086;&--1088;&--1075;&--1072;&--1085;&-- 1080;&--1095;&--1077;&--1089;&--1082;&--1080;&--1081; &--1089;&-- 1083;&--1086;&--1081; &--1086;&--1090;&--1076;&--1077;&--1083;&-- 1103;&--1077;&--1084; &--1080; &--1076;&--1080;&--1089;&--1090;&-- 1080;&--1083;&--1083;&--1080;&--1088;&--1091;&--1077;&--1084;. &-- 1044;&--1080;&--1089;&--1090;&--1080;&--1083;&--1103;&--1090; &-- 1085;&--1072;&--1075;&--1088;&--1077;&--1074;&--1072;&--1077;&-- 1084; &--1087;&--1088;&--1080; 240C &--1085;&--1072;&--1095;&-- 1080;&--1085;&--1072;&--1077;&--1090; &--1086;&--1073;&--1088;&-- 1072;&--1079;&--1086;&--1074;&--1099;&--1074;&--1072;&--1090;&-- 1100;&--1089;&--1103; &--1078;&--1077;&--1083;&--1090;&--1086;&-- 1077; &--1084;&--1072;&--1089;&--1083;&--1086;, accross &--1080; &-- 1090;&--1077;&--1084;&--1087;&--1077;&--1088;&--1072;&--1090;&-- 1091;&--1088;&--1091; &--1087;&--1086;&--1089;&--1090;&--1077;&-- 1087;&--1077;&--1085;&--1085;&--1086; &--1087;&--1086;&--1074;&-- Page 2 - 2009-05-22 22:36:02 C:\Documents and Settings\HP_Administrator.YOUR-4DACD0EA75\My Documents\GHB\Hive Ark\Ark\arch\forum\topic\topic_19.html 1099;&--1096;&--1072;&--1077;&--1084; &--1076;&--1086; 260C. &-- 1052;&--1072;&--1089;&--1083;&--1086; &--1084;&--1086;&--1078;&-- 1085;&--1086; &--1082;&--1088;&--1077;&--1089;&--1090;&--1072;&-- 1083;&--1080;&--1079;&--1086;&--1074;&--1072;&--1090;&--1100; &-- 1074;&--1099;&--1076;&--1077;&--1088;&--1078;&--1080;&--1074;&-- 1072;&--1085;&--1080;&--1077;&--1084; &--1074; &--1084;&--1086;&-- 1088;&--1086;&--1079;&--1080;&--1083;&--1082;&--1077; &--1085;&-- 1072; &--1087;&--1088;&--1086;&--1090;&--1103;&--1078;&--1077;&-- 1085;&--1080;&--1080; &--1089;&--1091;&--1090;&--1086;&--1082;. &-- 1057;&--1072;&--1084;&--1072; &--1087;&--1086; &--1089;&--1077;&-- 1073;&--1077; &--1082;&--1088;&--1080;&--1089;&--1090;&--1072;&-- 1083;&--1080;&--1079;&--1072;&--1094;&--1080;&--1103; &--1085;&-- 1077; &--1087;&--1088;&--1086;&--1080;&--1079;&--1086;&--1081;&-- 1076;&--1077;&--1090;, &--1073;&--1077;&--1088;&--1077;&--1090;&-- 1077; &--1083;&--1086;&--1078;&--1082;&--1091; &--1083;&--1086;&-- 1078;&--1080;&--1090;&--1077; &--1074; &--1084;&--1086;&--1088;&-- 1086;&--1079;&--1080;&--1083;&--1082;&--1091; &--1082;&--1086;&-- 1075;&--1076;&--1072; &--1086;&--1085;&--1072; &--1073;&--1091;&-- 1076;&--1077;&--1090; &--1090;&--1086;&--1081; &--1078;&--1077; &-- 1090;&--1077;&--1084;&--1087;&--1077;&--1088;&--1072;&--1090;&-- 1091;&--1088;&--1099; &--1095;&--1090;&--1086; &--1080; &--1088;&-- 1072;&--1089;&--1090;&--1074;&--1086;&--1088; &--1086;&--1087;&-- 1091;&--1089;&--1082;&--1072;&--1077;&--1090;&--1077; &--1077;&-- 1077; &--1074; &--1085;&--1077;&--1075;&--1086; , &--1101;&--1090;&-- 1086; &--1074;&--1099;&--1079;&--1086;&--1074;&--1077;&--1090; &-- 1085;&--1072;&--1095;&--1072;&--1083;&--1100;&--1085;&--1091;&-- 1102; &--1082;&--1088;&--1077;&--1089;&--1090;&--1072;&--1083;&-- 1080;&--1079;&--1072;&--1094;&--1080;&--1102; &--1080; &--1087;&-- 1086;&--1090;&--1086;&--1084; &--1086;&--1085;&--1072; &--1087;&-- 1088;&--1086;&--1076;&--1086;&--1083;&--1078;&--1080;&--1090;&-- 1089;&--1103;. &--1055;&--1088;&--1086;&--1080;&--1089;&--1093;&-- 1086;&--1076;&--1080;&--1090; &--1087;&--1077;&--1088;&--1077;&-- 1093;&--1086;&--1076; &--1086;&--1090; &--1086;&--1088;&--1072;&-- 1085;&--1100;&--1078;&--1077;&--1074;&--1086;&--1075;&--1086; &-- 1084;&--1072;&--1089;&--1083;&--1072; &--1082; &--1082;&--1088;&-- 1080;&--1089;&--1090;&--1072;&--1083;&--1072;&--1084; &--1089;&-- 1077;&--1088;&--1085;&--1086;&--1075;&--1086; &--1094;&--1074;&-- 1077;&--1090;&--1072; &--1084;&--1072;&--1089;&--1089;&--1086;&-- 1081; 180 &--1075; Methyl Phenyl Butenone. &--1054;&--1082;&--1080;&--1089;&--1083;&--1077;&--1085;&--1080;&-- 1077; Baeyer-Villiger. The reaction of the above unsaturated ketone with peracetic acid was first done by Boesken reported in Rec. Trav. Chim. 55, 786 (1936). There is some discussion of this also in US patent 3980708. Also see Organic Reactions Vols Page 3 - 2009-05-22 22:36:02 C:\Documents and Settings\HP_Administrator.YOUR-4DACD0EA75\My Documents\GHB\Hive Ark\Ark\arch\forum\topic\topic_19.html 9 & 43 I think. By following the directions in US Patent 5670661 you will get about 35% ketone based on the weight of the unsaturated ketone used. In that patent it is suggested that by recycling a higher percentage can be achieved. &--1042; &--1083;&--1080;&--1090;&--1088;&--1086;&--1074;&--1091;&-- 1102; &--1082;&--1086;&--1083;&--1073;&--1091; &--1076;&--1086;&-- 1073;&--1072;&--1074;&--1083;&--1103;&--1077;&--1084; 625 ml &-- 1083;&--1077;&--1076;&--1103;&--1085;&--1086;&--1081; &--1091;&-- 1082;&--1089;&--1091;&--1089;&--1085;&--1086;&--1081; &--1082;&-- 1080;&--1089;&--1083;&--1086;&--1090;&--1099; &--1080; 143 grms &-- 1053;&--1072;&--1090;&--1088;&--1080;&--1103; &--1087;&--1077;&-- 1088;&--1073;&--1086;&--1088;&--1072;&--1090;&--1072;. &--1050; &-- 1101;&--1090;&--1086;&--1084;&--1091; &--1076;&--1086;&--1073;&-- 1072;&--1074;&--1083;&--1103;&--1077;&--1084; 100 grms methyl phenyl butenone &--1089; &--1087;&--1086;&--1084;&--1077;&--1096;&--1080;&-- 1074;&--1072;&--1085;&--1080;&--1077;&--1084; &--1080; &--1085;&-- 1072;&--1075;&--1088;&--1077;&--1074;&--1072;&--1077;&--1084; &-- 1076;&--1086; 50C. &--1050;&--1086;&--1075;&--1076;&--1072; &-- 1073;&--1091;&--1076;&--1077;&--1090;&--1077; &--1085;&--1072;&-- 1075;&--1088;&--1077;&--1074;&--1072;&--1090;&--1100; &--1089;&-- 1090;&--1072;&--1088;&--1072;&--1081;&--1090;&--1077;&--1089;&-- 1100; &--1085;&--1077; &--1087;&--1077;&--1088;&--1077;&--1075;&-- 1088;&--1077;&--1090;&--1100;, &--1086;&--1076;&--1085;&--1072;&-- 1082;&--1086;, &--1077;&--1089;&--1083;&--1080; &--1089;&--1084;&-- 1077;&--1089;&--1100; &--1073;&--1091;&--1076;&--1077;&--1090; &-- 1089;&--1083;&--1080;&--1096;&--1082;&--1086;&--1084;
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