By Leonard, John; Lygo, B.; Procter, Garry
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Extra info for Advanced practical organic chemistry
7 in CHCl 3 ) Note that optical rotations are sometimes measured at frequencies other than that of the sodium-D line. If this is done, you will need to replace the “D” with the frequency used. 10. Chromatography data HPLC and/or GC are often used to determine purity or isomer ratios present in a mixture. When using these techniques, it is essential to record the conditions, the means of detection, and the type of column used as well as retention times. 11. Other data The preceding listed data are those that are essential for the characterization of most organic molecules.
Look for methods that involve the least hazardous reagents and techniques. Assess all the possible hazards associated with the reactions that you are planning to carry out as well as the chemicals you are using before carrying out a reaction. As well as toxicological issues, make sure that you are aware of any significant exotherms Chapter two: Safety 5 associated with the reaction and thermal instability issues associated with your chemicals. This is particularly important when you work on a larger scale.
Luche, L. Rodriguez-Hahn, P. Crabbe, J. Chem. , 1978, 601. Substance Amount Mol. wt. moles Equiv. 4 Source p. A21 Aldrich Method: The aldehyde (200 mg) and CeCl3 solution (2 ml) in MeOH (25 ml) were cooled to 0°C, then NaBH4 (27 mg) was added in batches (ca. 5 mg at a time) over 10 min. /EtOAc BB A23a (red/brown - vanilin) BB A23b (brown - vanilin) SM Rxn SM Rxn (b) After 30 min, TLC showed no starting material, so the MeOH was evaporated under reduced pressure. The residue was dissolved in CH2Cl2 (30 ml) and the solution washed with 10% aq.