ChemicalBook CAS DataBase List Benzo-15-crown-5

Benzo-15-crown-5 synthesis

12synthesis methods

Product Name:Benzo-15-crown-5
CAS Number:14098-44-3
Molecular formula:C14H20O5
Molecular Weight:268.31

benzo-15-crown-5 can be produced using Williamson synthesis reaction, featured by interaction between catechol (orto-dihydroxybenzene) and tetraethylene glycol dichloride (1,10-dichloro-3,6,9-trioxadecane) over sodium hydroxide in the n-butanol media (30-h inertatmosphere boiling). The yield of benzo-15-crown-5 produced by this method is 62%, with the basic substance's mass fraction of 95%.

DIETHYLENE GLYCOL BIS(2-CHLOROETHYL) ETHER

638-56-2
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$26.00/5g

120-80-9 Synthesis

120-80-9
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$13.00/25g

14098-44-3
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$28.00/1g

Yield:14098-44-3 82.097%

Reaction Conditions:

Stage #1:benzene-1,2-diol with sodium hydroxide in water;butan-1-ol
Stage #2:1,11-dichloro-3,6,9-trioxaundecane at 107; for 7 h;

Steps:

Benzo-15-crown-5 synthesis
General procedure 88 g (0.8 mole) catechol and 1200 mln-butanol was plased into a 2-liter ask equippedwith a mechanical stirrer, thermometer, watercondenser and dropping funnel was placed. Afterdissolution of the catechol by stirring, aqueous NaOHsolution (67.2 g NaOH to 80 ml H2O) was added.Mixing duration was 30 to 40 minutes. After 156.6 ml(0.8 mole) tetraethyleneglycol dichloride wasdripped through dropping funnel at 17 ml/min rate.The mixture was reuxed for 7 hours (107 0C). Afterthat, the fltrate was acidifed with concentratedhydrochloric acid, fltered off and ushed with wateruntil neutral reaction was reached. Upper organiclayer was put into round-bottom ask, treated withactivated carbon and fltered off. Then the fltrate wasboiled out using rotary evaporator, accompaniedby complete solvent distillation. The residue wasextracted with hexane, followed by producing whitetransparent crystals of benzo-15-crown-5

References:

Glushko, Valentina N.;Sadovskaya, Natalya Yu.;Kozhuhov, Vadim I.;Blokhina, Lidiya I.;Antropova, Irina A.;Petina, Ekaterina S.;Retiviov, Vasiliy M.;Melnikova, Ekaterina Yu. [Oriental Journal of Chemistry,2017,vol. 33,# 4,p. 1689 - 1697]

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