CAS number 108883 toluene -------------------------- MW 92.14 MP, ºC -93 BP, ºC 110.6 benzyl Chloride -------------------------- MW = 126.6 gm/mole Melting point -39 °C Boiling point 179 °C Phenylacetic acid -------------------------- MW 136.15 Melting point 76-77 °C Boiling point 265.5 °C ---------------------------- 28.6 grams toluene = .3104 mol benzylchloride .3104 mol = 39.29664 10.69664 grams gain 47.6% Ca(ClO)2 Ca(ClO)2 142.98 g/mol / 2 = 71.49 = 17.726 grams Cl Cl - 70.906[35.453] --------------------- 72.074 g/mol Ca(O)2 17 grams Ca(ClO)2 9.52 grams Ca(ClO2) Lithium 6.941 4 grams <> of Benz Chloride + 200<>mg of Li = Li breakdown to brown precipitate Solution turned brown .....Atectone in W/W addition causes Lithium to degrade compleatly Another of the 'wanted references': Tsuruta, Bull. Inst. Chem. Research, Kyoto Univ., vol. 31, 190-200 (1953) (in English); Chemical Abstracts vol 49, 6183b It seems that there was a chem abstract mistranslation. The synth actually uses chlorobenzene not benzyl chloride. The paper is entitled 'Michael and some related reactions' and is about 10 pages long. It's not practical to scan and post so I will just give the most important experimental section: ii. Ethyl acetate and benzyl sodium as reactants. Benzyl sodium was prepared according to Gilman's method*. Phenyl sodium prepared from 34 g (0.3 mol) of chlorobenzene and 13.8 g (0.6 atom) of sodium sand in 150 ml of dry toluene was refluxed on an oil bath for 3 hrs until the black colour of the precipitates turned to brownish black through reddish brown. The mixture was cooled to -4°C and was added 26.5 g (0.3 mol) of ethyl acetate in toluene in the course of 5 minutes under vigorous stirring. After 2 hrs stirring at about 0°C, t he mixture was allowed to stand overnight at room temp. and was added some methanol to dissolve the unreacted sodium present, acidified with aqueous acetic acid and the aqueous layer shaken with toluene. The toluene residue was fractionated at 17 mm. b.p.(17 mm) 130 - 155 °C 7 g (VIII) b.p.(17 mm) 195 - 200 °C 7 g (IX) An oil (VIII) readily crystallized by ice-cooling and reacted with semicarbazide to give crystals which melted at 187-188°C (recrystallized from alcohol-benzene mixture). Mixed melting point measurement with an authentic phenyl acetone semicarbazone assured (VIII) was phenyl acetone. The viscous oil (IX) was not distinctly identified, but it is very likely that (IX) is methyl dibenzyl carbinol. * H. Gilman, H. A. Pacevitz & O. Baine : J. Am. Chem. Soc, 62, 1514(1940) If Aurelius is correct which seems rather likely than the result of conducting this reaction with benzyl sodium would be phenyl-2-butanone, not phenyl-2-propanone. SWIL doesn't have much spare time but felt that you needed to be told about this misprint error Electro chemistry ------------------ http://www.freepatentsonline.com/4904370.html conversion of Benzylchloride to benzyliodine A Photoelectrochemical Fixation of Carbon Dioxide. Spontaneous Up Quality Conversion of Organic Compound Jo-ji Ueda1), Seiichiro Nakabayashi1), Jun-ichi Ushizaki1) and Kohei Uosaki1) 1) Physical Chemistry Laboratory, Department of Chemistry, Faculty of Science, Hokkaido University (Received June 30, 1993) A photosynthetic semiconductor electrochemical cell with Mg electrode as a sacrificial anode was assembled. This photoelectrochemical cell spontaneously fixes carbon dioxide into organic molecule such as benzyl chloride to form phenyl acetic acid which costs 7.5 times more than the sources. Among the semiconductor electrodes investigated, p-GaP showed highest current efficiency, 47%. electro chemical phenylacetic acid http://www.jstage.jst.go.jp/article/cl/22/10/22_1747/_article http://cat.inist.fr/?aModele=afficheN&cpsidt=18264890 Very nice text eplaing the use of nano particals for CO2 fixing leading to 34% yeilds of Phenylacetic acid and the rest returnes to toluene. bad yeilds but with impovements could prove useful being as the only side product can be rechlorinated http://www.rsc.org/ej/P2/1997/a604515d.pdf Phenylacetic acid ---------------------- cabonication of benzyl chloride http://www.bjb.dicp.ac.cn/jngc/2005/2005-14-01-0040-7.pdf