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22nd August 2013 @ 10:15

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Reaction information

*#Reaction file  
CSRxnsScheme_109b.cdx
*Reaction file type CDX
*Procedure  Perchloric acid (0.10 mL of a 70% aq. solution, 1.2 mmol) was added dropwise to ethyl-3,5-(bisbenzyloxy)benzene (224 mg, 1.0 mmol) in octanoic anhydride (1.80 mL, 6.0 mmol).  The reaction mixture was stirred at room temperature for 4 h, extracted with ether (35 mL), washed with sat. aq. NaHCO3 solution (5 × 50 mL), dried (MgSO4), filtered and the solvent removed in vacuo to give the crude product as a green oil (2.38 g). Purification by column chromatography (SiO2, hexane/Et2O 3:1) gave an orange oil which was dissolved in ether (50 mL) and washed with 2 M aq. NaOH solution (50 mL) to remove excess octanoic acid.  The organic extract was dried (MgSO4), filtered and the solvent removed in vacuo to give the title compound as an orange oil (675 mg, 45%).
*Yield (%)  45
*Type of Yield Isolated product yield
Reference(s)  
AH Thesis_2011_pp71.pdf
AH Thesis_2011_pp168-175.pdf
Further information  Compound 109b: 3,5-(Bisbenzyloxy)cytosporone B

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Overall reaction? True
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Attached Files
AH Thesis_2011_pp71.pdf
CSRxnsScheme_109b.cdx
AH Thesis_2011_pp168-175.pdf