2-(Hydroxymethyl)-12-crown 4-ether

CLEAR COLOURLESS VISCOUS LIQUID

2-Hydroxymethyl-12-crown-4 can be used:

• To prepare an ester of lasalocid with crown ether to study its complex formation with monovalent cations.
• To prepare hydrogel adsorbents for potential usage in the recovery of lithium-ions from seawater.
• As a starting material in the synthesis of metal-free phthalocyanines and metallophthalocyanines.

Ethylene oxide is important or critical to the production of detergents, thickeners, solvents, plastics, and various organic chemicals such as ethylene glycol, ethanolamines, simple and complex glycols, polyglycol ethers and other compounds.

Purify it by chromatography on Al2O3 with EtOAc as eluent to give a hygroscopic colourless oil, which is distilled under high vacuum and is distilled in vacuo. It has IR: 3418 (OH) and 1103 (COC) cm-1, NMR: max 3.70s. [Kimura et al. J Chem Soc, Chem Commun 492 1983, Pugia et al. J Org Chem 52 2617 1987.] S -(-)-5-Hydroxymethyl -2(5 H )-furanone [78508-96 -0] M 114.1, 39 -42o, 40 -44o , b 1 3 0o/0.3mm, [ ] 546 -180o, [ ] D -148o (c 1.4, H2O). It is purified by chromatography on Silica gel using hexane/EtOAc (1:1) to give a colourless oil which is distilled using a Kügelrohr apparatus, and the distillate crystallises on cooling. It has RF 0.51 on Whatman No 1 paper using pentan-1-ol and 85% formic acid (1:1) and developing with ammoniacal AgNO3. [Boll Acta Chem Scand 22 3245 1968, NMR: Oppolzer et al. Helv Chim Acta 68 2100 1985, Beilstein 18 III/IV 56, 18/1 V 54.]