Diethylene glycol monomethyl ether synthesis
- Product Name:Diethylene glycol monomethyl ether
- CAS Number:111-77-3
- Molecular formula:C5H12O3
- Molecular Weight:120.15
![Phenol, 4-[[2-(2-methoxyethoxy)ethoxy]methyl]-](/CAS/20210305/GIF/115319-74-9.gif)
115319-74-9
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111-77-3
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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
109-86-4
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107-07-3
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111-77-3
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111-46-6
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123-91-1
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111-77-3
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111-96-6
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13752-97-1
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111-77-3
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112-35-6
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111-77-3
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111-96-6
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