ChemicalBook CAS DataBase List Diethylene glycol monomethyl ether

Diethylene glycol monomethyl ether synthesis

10synthesis methods

Product Name:Diethylene glycol monomethyl ether
CAS Number:111-77-3
Molecular formula:C5H12O3
Molecular Weight:120.15

A by-product in the manufacture of ethylene glycol monomethyl ether (Arctander, 1969).

Phenol, 4-[[2-(2-methoxyethoxy)ethoxy]methyl]-

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Yield:111-77-3 97%

Reaction Conditions:

with iron(III) chlorideProduct distribution / selectivity;

Steps:

7

With PSB ethers in hand, the deprotection was investigated using conditions identified previously in our laboratory. Tamao-type oxidation of aryl ethers in 3a and 3b provides the deprotected phenols (2a and 2b) in one step (Table 2, entries 1 and 2). Intermediate PHB ethers 4a and 4b undergo solvolysis during the course of the reaction.In the aliphatic ether cases (3c-e), the labile PHB ethers (4c-e) were isolated and then cleaved using FeCl₃(entries 3-5, 7) or DDQ (2,3-dichloro-5,6-dicyano-1,4-benzoquinone; entry 6) to give alcohols 2c-e. Alternatively, Woerpel's more rigorous carbosilane oxidation protocol also affords the PHB ethers (4c and 4d, entries 6 and 7). Such conditions are not expected to tolerate pendant silyl ether PGs, but they do afford excellent yields after a relatively simple purification. PSB ethers can also be removed by hyrdogenolysis (entry 8).

References:

US7754909,2010,B1 Location in patent:Page/Page column 4-5; 10