The preparation of ortho and para hydroxybenzyl alkyl ethers

Jonge, J. de; Bibo, B. H.

doi:10.1002/recl.19550741202

Cited by 14 publications

(3 citation statements)

References 5 publications

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“…This material gave an IR spectrum quite similar to that reported by Langoor and van der Maas . The original synthesis of this compound gave it a melting point of −1 °C . A single crystal was eventually obtained by prolonged storage at −80 °C.…”

Section: Background and Resultssupporting

confidence: 74%

“…39 The original synthesis of this compound gave it a melting point of -1 °C. 40 A single crystal was eventually obtained by prolonged storage at -80 °C. The O-H stretching region of the IR spectrum of this undoubtedly pure 2-methoxymethylphenol in CCl 4 is shown in Figure 9.…”

Section: O-mentioning

confidence: 99%

“…First, calculations of the intramolecular HB strength in the structurally related 2-hydroxybenzyl alcohol implied that the “free” phenol concentration in 2-methoxymethylphenol should be negligible. Second, the synthesis of this phenol has been shown to give o -cresol as a major side product, together with other products that would also show “free” OH groups …”

Section: Introductionmentioning

confidence: 99%

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Intramolecular and Intermolecular Hydrogen Bond Formation by Some Ortho-Substituted Phenols: Some Surprising Results from an Experimental and Theoretical Investigation

et al. 2009

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The effects produced by addition of various concentrations of the strong hydrogen bond (HB) acceptor, dimethyl sulfoxide (DMSO), on the OH fundamental stretching region of the IR spectra of several o-methoxy, o-nitro, and o-carbonyl phenols in CCl(4) are reported. In most of these phenols the intramolecular HB is not broken by the DMSO. Instead, the DMSO acts as a HB acceptor to the intramolecular HB forming a bifurcated intra/intermolecular HB. For o-methoxyphenols the bifurcated HBs are observed as new IR bands at much lower wavenumbers (Deltanu(OH) approximately -300 cm(-1)) than the band due to their intramolecular HB. The formation of bifurcated HBs and the large frequency shift of their OH bands in o-methoxyphenols are well reproduced by theoretical modeling. In contrast to the o-methoxyphenols DMSO has little effect (other than causing some broadening) on the intramolecular HB OH bands of o-nitro and o-carbonyl phenols, with the single exception of 2,4-dinitrophenol. In this case, but not for 2,4-diformylphenol, the intramolecular HB OH band decreases as the DMSO concentration increases and a new absorption grows in at lower wavenumbers, indicating that DMSO can break this intra-HB and form an inter-HB, a result well reproduced by theory. Although DMSO has little effect on the O-H stretching band of 2-nitrophenol, theory indicates extensive formation (90%) of bifurcated HBs with OH stretching bands at slightly higher wavenumbers (Deltanu(OH) approximately +20 cm(-1)) than that for the intramolecular HB OH group and 10% of a "simple" intermolecular HB in which the intramolecular HB has been broken. Theory also indicates that, with DMSO, 2-formylphenol also forms a bifurcated HB (Deltanu(OH) approximately +150 cm(-1)), whereas 2,4-diformylphenol forms both intermolecular HBs (Deltanu(OH) approximately -130 cm(-1)) and bifurcated HBs (Deltanu(OH) approximately +165 cm(-1)). The IR spectrum of 2-methoxymethylphenol shows that although an intramolecular HB conformer is dominant there is a small percentage of a "free" OH, non-HB conformer (2.1% in CCl(4), 1.5% in cyclohexane). These results are quantitatively reproduced by theory. We conclude that theory can provide important insights into the formation and structure of inter, intra, and bifurcated HBs, and into their OH stretching frequencies, that are not always revealed by IR studies alone.

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Section: Background and Resultssupporting

confidence: 74%

Section: O-mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Intramolecular and Intermolecular Hydrogen Bond Formation by Some Ortho-Substituted Phenols: Some Surprising Results from an Experimental and Theoretical Investigation

et al. 2009

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Über die Reduktion aromatischer Diazoverbindungen mit äthern, 1.3‐Dioxolanen und tertiären Aminen

et al. 1958

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Es wird die Reduktion aromatischer Diazoverbindungen zu den entspr. ArH-Verbindungen in wäß-riger, acetat-gepufferter Lösung unter Verwendung der mit Wasser mischbaren Äther: Dioxan, Tetrahydrofuran, Glykol-dimethyläther und 1.3-Dioxolan beschrieben. Als Oxydationsprodukte der Äther entstehen deren Monoxy-Verbindungen. Der Reaktionsmechanismus wird erörtert. Die Reaktion der Aryldiazonium-fluoroborate mit Isobornyl-alkyläthern in Acetonitril-Lösung liefert neben den ArH-Verbindungen an Stelle der erwarteten, bekannten O-Alkyl-campheroxonium-fluoroborate unter Mitbeteiligung des Acetonitrils Nitrilium-fluoroborate. Bei der Reduktion verschiedener Diazonium-fluoroborate mit 2-Methyl-und 2-Phenyl-1.3-dioxolan konnten die neben den ArH-Verbindungen als Oxydationsäquivalente entstehenden Carbonium-Oxonium-fluoroborate in guten Ausbeuten isoliert werden. Tertiäre Amine reduzieren die Diazonium-fluoroborate in Acetonitril-Lö-sung zu den entspr. ArH-Verbindungen unter Übertragung eines a-ständigen Hydrid-Ions und Bildung von Carbonium-lmmonium-fluoroboraten. Einleitung

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Fragmentierung und Indophenolbildung bei O ‐Alkyl‐ N ‐(4‐hydroxyphenyl)hydroxylaminen

Rolf

Heesing

1974

Chem. Ber.

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Die säurekatalysierte Spaltung der NO‐Bindung in O‐Alkyl‐N‐(4‐hydroxyphenyl)hydroxylaminen 1c wird durch den Elektronendonator‐Effekt der Hydroxygruppe stark erleichtert. In einer schnellen Folgereaktion entstehen Indophenole. Abfangversuche zeigen, daß ihre Bildung auf einer Kondensation des intermediär gebildeten Chinonimins mit noch nicht fragmentierter Ausgangsverbindung beruht.

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The preparation of ortho and para hydroxybenzyl alkyl ethers

Abstract: The preparation of some alkyl ethers of ortho and para hydroxybenzyl alcohol is described.

Cited by 14 publications

References 5 publications

Intramolecular and Intermolecular Hydrogen Bond Formation by Some Ortho-Substituted Phenols: Some Surprising Results from an Experimental and Theoretical Investigation

Intramolecular and Intermolecular Hydrogen Bond Formation by Some Ortho-Substituted Phenols: Some Surprising Results from an Experimental and Theoretical Investigation

Über die Reduktion aromatischer Diazoverbindungen mit äthern, 1.3‐Dioxolanen und tertiären Aminen

Fragmentierung und Indophenolbildung bei O ‐Alkyl‐ N ‐(4‐hydroxyphenyl)hydroxylaminen

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