A rapid, simple, and mild procedure for alkylation of phenols, alcohols, amides and acids

Johnstone, R. A. W.; Rose, Malcolm E.

doi:10.1016/0040-4020(79)87035-0

Cited by 356 publications

(187 citation statements)

References 16 publications

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“…KOH in polar aprotic solvents has been used for the alkylation of carboxylic acids, amides and phenols with reactive alkyl halides under mild conditions, providing the corresponding esters, Nalkyl amides and aryl ethers in good yields. 25 Accordingly, alkylation of kaurenoic acid 1 with a combination of methyl iodide and KOH in acetone resulted in a clean transformation to methyl kaurenoate 2, isolated in 89% yield (not optimized). The potential generality of this reaction was attested by extending the conditions to alkyl bromides, leading to the respective kaurenoates 9-14 in moderate to high yields (Scheme 3).…”

Section: Resultsmentioning

confidence: 99%

A simple synthesis of kaurenoic esters and other derivatives and evaluation of their antifungal activity

Boeck

Sá

Souza

et al. 2005

J. Braz. Chem. Soc.

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Este trabalho descreve a preparação de ésteres e amidas derivados do ácido caurenóico e a avaliação da atividade antifúngica frente a cepas padronizadas de fungos patogênicos. Ésteres alquílicos e benzílicos foram obtidos com bons rendimentos, sob condições brandas, a partir da esterificação do ácido caurenóico com haletos de alquila em KOH-acetona. Todos os compostos sintetizados foram submetidos aos testes de inibição contra leveduras, hifomicetos e dermatófitos, mas somente o ácido caurenóico e os derivados contendo um grupo carboxilato livre apresentaram atividade moderada frente a dermatófitos.Representative esters derived from kaurenoic acid were prepared in order to evaluate their antifungal properties. Alkyl and substituted benzyl esters were obtained in good yield under mild conditions by esterification of kaurenoic acid with the corresponding alkyl halide in KOH-acetone. All synthesized compounds were tested for antifungal properties against pathogenic yeasts, hialohyphomycetes and dermatophytes. Kaurenoic acid and derivatives containing a free carboxyl group were moderately active against dermatophytes.

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Section: Resultsmentioning

confidence: 99%

A simple synthesis of kaurenoic esters and other derivatives and evaluation of their antifungal activity

Boeck

Sá

Souza

et al. 2005

J. Braz. Chem. Soc.

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“…Polarimetric response was detected at 675 nm, and is only reported when an unambiguous assignment of the elution order was possible for a standard run. (R,R )-N-allyl-O,OV-bis(dimethylbenzoyl) tartaric acid monoamide (8). Allylamine (2.15 ml 2.2 eq.)…”

Section: Synthesismentioning

confidence: 99%

“…8 Finely ground KOH (17 g) was stirred in 40 ml DMSO for 5 min at room temperature (RT), then cooled on ice. 8 Acetal 4 (12.05 g, 37.9 mmol) was added to the cooled and stirred slurry followed by MeI (10 ml, 4 eq.). The resulting warm, clear brown solution was left to cool to RT.…”

Section: Synthesismentioning

confidence: 99%

Effects from hydrogen bonding and rigidity on selectivity in tartaric acid‐based chiral selectors for enantioselective liquid chromatography

Oxelbark

Sellén

2003

Chirality

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Tartaric acid-based selectors 1 ((R,R)-O,OV-Bis(dimethylbenzoyl)-N,NVdiallyl-N,NV-dimethyl tartaramide) and 2 ((R,R)-N-allyl-O,OV-bis(dimethylbenzoyl) tartarimide) were synthesized, immobilized on silica, and evaluated as chiral stationary phases in enantioselective chromatography. Comparison with the commercially available column Kromasil-CHI-1, based on selector 3 ((R,R)-O,OV-Bis(dimethylbenzoyl)-N,NV-diallyl tartaramide) resulted in the conclusion that amide NH functions are essential to chiral recognition on this sorbent. Furthermore, NH functions contribute significantly to retention of analytes except for alcohols. It was also found that flexibility of the benzoyl moieties is essential to selectivity. KEY WORDS: chiral chromatography; tartar amide; tartar imide; CD spectroscopy Separation of racemates into pure enantiomers by enantioselective chromatography has become an increasingly important alternative to asymmetric synthesis in the pharmaceutical industry. This is mainly due to fast method development and the possibility to rapidly produce limited amounts of both enantiomers for biological testing by preparative enantioselective chromatography. 1 This new strategy relies on the rapid development of chiral stationary phases for liquid chromatography over the last 20 years, which is still continuing. Enantioselective chromatography is now a state of the art technique available in many research labs, but still there is a demand for new chiral sorbents. The big concerns in the development of new chiral stationary phases are largely about selectivity (i.e., general selectivity) and robustness. Chemical stability is important in order to permit the use of solvents that dissolve analytes easily, thus maximizing throughput in preparative applications. So far, the general selectivity displayed by polysaccharide-based sorbents, 2 -4 has been associated with low tolerance to, e.g., halogenated solvents, because selectors are not covalently bonded to the silica support. Moreover, covalent bonding of these phases is associated with a lowering of selectivity. 5 On the other hand, different types of covalently bonded phases with high robustness typically display a somewhat lower general selectivity. Development of new chiral stationary phases is thus of great importance and an improved understanding of the underlying separation mechanisms of available selectors is of great importance for this.

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“…1,4-Di-n-octyloxybenzene (6) was synthesized in 74% yield from commercially available p-hydroquinone using the method of Johnstone and Rose. 21 All spectra and the melting point were as reported. 22 The bromomethylation of 6 using a method similar to that reported 23,24 carried out in acid-washed glassware using paraformaldehyde and KBr in acetic acid produced di-noctyloxy-1,4-bis(bromomethyl)benzene (7) in 73% yield.…”

Section: Resultsmentioning

confidence: 99%

Systematic Study of the Effects of Naphthalene and Anthracene Substitution on the Properties of PPV Derivative Conjugated Systems

Lynch¹,

O’Neill²,

Bradley³

et al. 2007

Macromolecules

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The systematic synthesis of poly(phenylvinylene) (PPV) derivatives by the Wittig-Horner reaction is reported. The phenyl units of the PPV structure are methodically substituted by naphthyl and anthryl units to form a homologous series of structures. The 2,6 attachment of the vinylene linkage on the anthryl ring provides novel structures that have not been reported before due to their synthetic inaccessibility. The introduction of naphthyl units results in a hypsochromatic shift in the absorption and emission spectra, while the introduction of anthryl units leads to a bathochromatic shift relative to the naphthalene structures. The observed structural variation of the spectroscopic properties is explained in terms of a combination of the increased conjugation of the substituent acene units and the decreased electronic contribution across the vinyl linkage.

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A rapid, simple, and mild procedure for alkylation of phenols, alcohols, amides and acids

Cited by 356 publications

References 16 publications

A simple synthesis of kaurenoic esters and other derivatives and evaluation of their antifungal activity

A simple synthesis of kaurenoic esters and other derivatives and evaluation of their antifungal activity

Effects from hydrogen bonding and rigidity on selectivity in tartaric acid‐based chiral selectors for enantioselective liquid chromatography

Systematic Study of the Effects of Naphthalene and Anthracene Substitution on the Properties of PPV Derivative Conjugated Systems

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