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22nd August 2013 @ 10:13

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Reaction information

*#Reaction file  
CSRxnsScheme_108b.cdx
*Reaction file type CDX
*Procedure Diazomethane in dry ether [produced by addition of KOH (2.97 g, 53.0 mmol) in 96% ethanol (35 mL) to Diazald® (2.91 g, 13.6 mmol) in dry ether (50 mL)] was distilled into a flask containing a solution of 3,5-(Bisbenzyloxy)benzoyl chloride  (1.19 g, 3.4 mmol) in dry ether (15.0 mL) at −78 °C.  The reaction mixture was stirred at room temperature with a dry ice condenser attached for 2 h and for a further 1 h without dry ice in the condenser to remove excess diazomethane.  The solvent was removed in vacuo to give a pale yellow solid which was refluxed in ethanol (20 mL) with Ag2O (200 mg) for 1 h.  Further Ag2O (200 mg) was added and refluxing continued for a further 2 h.  The reaction mixture was filtered through celite and the solvent removed in vacuo to give the crude product as an orange oil (1.204 g). Purification by column chromatography (SiO2, hexane/Et2O 4:1) gave the title compound as a colourless oil (796 mg, 62%).
*Yield (%)  62
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp71.pdf
AH Thesis_2011_pp168-175.pdf
Further information  Compound 108b: Ethyl-3,5-(bisbenzyloxy)benzene

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Attached Files
AH Thesis_2011_pp71.pdf
CSRxnsScheme_108b.cdx
AH Thesis_2011_pp168-175.pdf