3,6,9,12,15,18-Hexaoxanonadecan-1-ol

Hexaethylene glycol monomethyl ether is a hydroxypolyether. It derives from a hexaethylene glycol.

2-(2-(2-Methoxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate (Al, 1.0 g, 3.14 mmol) was added with stir to triethylene glycol (2.10 mL, 15.7 mmol). Potassium hydroxide (510 mg, 9.42 mmol) was ground into a powder and added to the reaction and the mixture refluxed at 100°C for 12 hours, upon which the reaction was diluted with water (50 mL) and extracted with DCM. The organic layers were combined, dried over sodium sulfate, and concentrated under reduced pressure to obtain 2, 5, 8, 1 l, 14, 17-hexaoxanonadecan-19-ol as a yellow oil in 69percent yield.The synthesis of compound 3 is shown in Figure 5. Synthesis of compound 3 began by coupling tosylate (6) to triethylene glycol (16) under basic conditions to yield hexaethylene glycol monomethyl ether (17) in 65percent yield. Hexaethylene glycol monomethyl ether (17) was then converted to the corresponding tosylate (18) in 77percent yield, followed by conversion to the azide. The azide was reduced to the corresponding amine (19) via a hydrogenation over activated palladium on carbon in 45percent yield. The amine was coupled to cyanoacetic acid using 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDC) in 80percent yield to give the cyano-acetamide (20). The resulting amide (20) was coupled with previously synthesized piperidine-naphthalene (12) to give compound 3 via Knovenagel condensation in 61percent yield.D. Hexaethylene Glycol Monomethvl Ether A 50percent wet paste of 10percent palladium on carbon (0.71 g, 5 molpercent) was charged to a nitrogen purged flask. A solution of hexaethylene glycol monomethyl monobenzyl ether (BnO-6EG-OMe; 2.66g, 6.88 mmol) in tetrahydrofuran (26.6 mL) was added. The mixture was stirred under an atmosphere of hydrogen for 90 minutes. The mixture was filtered through celite to remove the catalyst. The solids were washed with tetrahydrofuran (20 mL). The filtrate was concentrated to dryness to give hexaethylene glycol monomethyl ether (2.01 g, 99percent theory). (Using the synthesis of M-PEG 7 as an example). Under the atmosphere of N

Molecular Weight:296.36
XLogP3:-1.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:17
Exact Mass:296.18350323
Monoisotopic Mass:296.18350323
Topological Polar Surface Area:75.6
Heavy Atom Count:20
Complexity:169
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes