- Heat under reflux for 4 hours a solution of 3 g (0.0165 mol) of undec-10-ynoic acid in 240 ml of glacial acetic acid containing 13 ml of concentrated sulphuric acid and 1.4 g of mercury(n) acetate.
- Dilute the dark coloured solution with 300 ml of water, filter and extract the solution with dichloromethane using a continuous extraction apparatus(1).
- Wash the dichloromethane extract carefully with distilled water until the washings are neutral, dry the extract and evaporate on a rotary evaporator.
- Recrystallise the solid residue from light petroleum (b.p. 60-80 °C) using a little decolourising charcoal. The yield of keto-acid, m.p. 56-57 °C, is 1.65 g (50%).
Notes to keep in mind:
1. Batchwise extraction leads to the formation of
stable emulsions which frequently take several days to break. When filling the
continuous extraction apparatus, care should be taken to avoid forming an
emulsion.
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