The Cleavage of Ethers.

Burwell, Jr. Robert L.

doi:10.1021/cr60170a003

Cited by 277 publications

(125 citation statements)

References 126 publications

(214 reference statements)

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“…Although the dark color suggested the presence of quinones, concentrated H 2 SO 4 has been reported to convert aryl methyl ethers to phenols, which may further complicate the product distribution. [16] Interestingly, HBr (6 m) cleanly produced bisphenol 5 in 67 % yield at room temperature. This is probably the result of the enhanced reactivity of the intermediate carbocation due to the greater polarizability of bromide compared to chloride.…”

Section: Synthesis Of Bisphenolsmentioning

confidence: 99%

Synthesis of Renewable Bisphenols from Creosol

2011

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A series of renewable bisphenols has been synthesized from creosol (2-methoxy-4-methylphenol) through stoichiometric condensation with short-chain aldehydes. Creosol can be readily produced from lignin, potentially allowing for the large scale synthesis of bisphenol A replacements from abundant waste biomass. The renewable bisphenols were isolated in good yields and purities without resorting to solvent-intense purification methods. Zinc acetate was shown to be a selective catalyst for the ortho-coupling of formaldehyde, but was unreactive when more sterically demanding aldehydes were used. Dilute HCl and HBr solutions were shown to be effective catalysts for the selective coupling of aldehydes in the position meta to the hydroxyl group. The acid solutions could be recycled and reused multiple times without decrease in activity or yield.

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Section: Synthesis Of Bisphenolsmentioning

confidence: 99%

Synthesis of Renewable Bisphenols from Creosol

2011

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“…In particular, the 1 : 1/3 molar mixtures gave total AH values ~--90 k J/mole PGE, i.e. a value double that found in the isothermal test at 603 K. It is very probable that the higher temperatures reached in dynamic measurements promote not only the reaction of the less acid hydrogens, but also reactions of rearrangement and/or scission of the ether bond [5,6].…”

Section: Discussionmentioning

confidence: 73%

Differential scanning calorimetry study of reactions of phenyl glycidyl ether with phosphoric acid

Severini

Gallo

Audisio³

1987

Journal of Thermal Analysis

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The reactions of phenyl glycidyl ether (PGE) with phosphoric acid in three molar ratios have been studied by means of DSC alone. The results obtained from isothermal measurements are as follows: AH = -91.0 k J/mole PGE (1 -1 molar ratio); AH = -100.5 kJ/mole PGE (1 : ]molar ratio).The DSC curves obtained from dynamic experiments are multipeaked and give AH values higher than those obtained from isothermal measurements. These results can be explained by taking into account the acid concentration, the different reactivities of the hydrogens of the phosphoric acid and the possibility that secondary reactions occur. Analogous values for the reaction of an epoxide with inorganic polybasic acids are not to be found.The aim of this work was to study, by means of DSC only, the reaction of phosphoric acid with a simple epoxide compound, such as phenyl glycidyl ether. ExperimentalThe following reactants were used: phenyl glycidyl ether 95% (Fluka); orthophosphoric acid 99% (Carlo Erba). These were used without further purification.

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“…16 However, no isolable product was observed in this reaction. Our continued attempts with Lewis acids such as BF 3 .OEt 2 , 17 AlCl 3 , 18 and trimethylsilyl iodide 19 afforded either mixture of products resulting from the benzylic cleavage with no isolable amount of the desired product or the recovery of the starting material.…”

Section: Resultsmentioning

confidence: 99%

Chiral synthesis of (2S,3S)‐2‐(2‐morpholin‐2‐yl‐2‐phenylmethoxy)phenol

et al. 2004

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Resolution of (2RS,3RS)-2-[alpha-(2-methoxymethoxyphenoxy)phenylmethyl]morpholine, 11, with (+) mandelic acid led to the formation of (+)-(2S,3S)-2-[alpha-(2-methoxymethoxyphenoxy)phenyl methyl] morpholine (11a). Compound 11 was synthesized in seven steps from (2RS,3RS)-cinnamyl alcohol-2,3-epoxide (4), with an overall yield of 17%. Cleavage of the methoxymethyl group of the Fmoc derivative 12 with catalytic amounts of p-toluenesulfonic acid in methanol afforded (+)-(2S,3S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol 2. The synthetic utility as well as the configuration of compound 2 has been demonstrated by converting (S,S)-2-(2-morpholin-2-yl-2-phenylmethoxy)phenol 2 to (2S,3S)-2-[alpha-(2-ethoxyphenoxy)phenylmethyl]morpholine (1) and (2S,3S)-2-(2-methoxyphenoxy) benzyl)morpholine (16), two potential norepinephrine reuptake inhibitors under clinical evaluation.

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The Cleavage of Ethers.

Cited by 277 publications

References 126 publications

Synthesis of Renewable Bisphenols from Creosol

Synthesis of Renewable Bisphenols from Creosol

Differential scanning calorimetry study of reactions of phenyl glycidyl ether with phosphoric acid

Chiral synthesis of (2S,3S)‐2‐(2‐morpholin‐2‐yl‐2‐phenylmethoxy)phenol

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