Org. Synth. 1930, 10, 94
Submitted by M. Nierenstein and D. A. Clibbens.
Checked by Roger Adams and F. E. Kendall.
In a 5-l. flask fitted with a reflux condenser, a solution containing 200 g. (1.8 moles) of resorcinol, 1 kg. (9.9 moles) of potassium acid carbonate (Note 1), and 2 l. of water (Note 2) is heated slowly on a steam bath for four hours. The flask is then placed over a flame and refluxed vigorously for thirty minutes; a rapid stream of carbon dioxide is passed through the solution during this heating process.
While still hot the solution is acidified by adding 900 cc. of concentrated hydrochloric acid (sp. gr. 1.19) from a separatory funnel with a tube delivering the acid to the bottom of the flask; this prevents the formation of a layer of acid over the unneutralized solution. The flask is allowed to cool to room temperature and is then chilled in an ice bath. The resorcyclic acid crystallizes in prisms which are almost colorless but which, on exposure to air, turn pink owing to contamination with a small amount of resorcinol. The yield of crude acid is 225 g. By extracting the mother liquor with ether several times, 35 g. of resorcylic acid and some unchanged resorcinol can be recovered. The resorcylic acid is extracted from the ether by shaking with an aqueous solution of sodium bicarbonate. The aqueous solution is acidified with hydrochloric acid and again extracted withether. The ether is then evaporated, leaving the resorcylic acid, which is usually highly colored and must be recrystallized several times from boiling water and charcoal to remove the color.
The combined yield of crude acid (260–270 g.) is dissolved in 1 l. of water, boiled with about 25 g. of Norite, filtered through a heated filter, and crystallized by placing in an ice-salt freezing mixture and stirring vigorously. A finely crystalline, colorless product is obtained in this way. If the acid is allowed to crystallize slowly the crystals are somewhat colored. The yield of pure resorcylic acid melting at 216–217° is 160–170 g. (57–60 per cent of the theoretical amount) (Note 3).
Instead of potassium acid carbonate
, the sodium salt in corresponding quantity may be used.
If less than ten parts of water to one of resorcinol
is used, the yield is diminished.
The air-dried crystals lose at 110° a quantity of water corresponding to a half mole of water of crystallization.
The method of preparing β-resorcylic acid
described above is a modification1
of the procedure given by Bistrzycki and Kostanecki.2
A more rapid but less efficient variant of this procedure has been described.3
This preparation is referenced from:
Chemical Abstracts Nomenclature (Collective Index Number);
potassium acid carbonate
hydrochloric acid (7647-01-0)
sodium bicarbonate (144-55-8)
carbon dioxide (124-38-9)
β-Resorcylic acid (89-86-1)
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