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2-Naphthol

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Thomas K. Wood – One of the best experts on this subject based on the ideXlab platform.

  • Phenol and 2-Naphthol production by toluene 4-monooxygenases using an aqueous/dioctyl phthalate system
    Applied Microbiology and Biotechnology, 2005
    Co-Authors: Ying Tao, William E. Bentley, Thomas K. Wood

    Abstract:

    A two-phase system is developed here for converting: (1) benzene to phenol and (2) naphthalene to 2-Naphthol, using whole cells expressing wild-type toluene 4-monooxygenase (T4MO) and the alpha subunit variant TmoA I100A from Pseudomonas mendocina KR1. Using the T4MO TmoA I100A variant, the solubility of naphthalene was enhanced and the toxicity of the naphthols was prevented by the use of a water/dioctyl phthalate (80:20, vol%) system which yielded 21-fold more 2-Naphthol. More than 99% 2-Naphthol was extracted to the dioctyl phthalate phase, dihydroxynaphthalene formation was prevented, 92% 2-Naphthol was formed, and 12% naphthalene was converted. Similarly, using 50 vol% dioctyl phthalate, an initial concentration of 3.0 g l−1 (39 mM), and wild-type T4MO, a 51±9% conversion of benzene was obtained and phenol was produced at a purity of 97%. Relative to the one-phase system, there was a 12-fold reduction in the formation of the byproduct catechol.

  • phenol and 2 naphthol production by toluene 4 monooxygenases using an aqueous dioctyl phthalate system
    Applied Microbiology and Biotechnology, 2005
    Co-Authors: Ying Tao, William E. Bentley, Thomas K. Wood

    Abstract:

    A two-phase system is developed here for converting: (1) benzene to phenol and (2) naphthalene to 2-Naphthol, using whole cells expressing wild-type toluene 4-monooxygenase (T4MO) and the alpha subunit variant TmoA I100A from Pseudomonas mendocina KR1. Using the T4MO TmoA I100A variant, the solubility of naphthalene was enhanced and the toxicity of the naphthols was prevented by the use of a water/dioctyl phthalate (80:20, vol%) system which yielded 21-fold more 2-Naphthol. More than 99% 2-Naphthol was extracted to the dioctyl phthalate phase, dihydroxynaphthalene formation was prevented, 92% 2-Naphthol was formed, and 12% naphthalene was converted. Similarly, using 50 vol% dioctyl phthalate, an initial concentration of 3.0 g l−1 (39 mM), and wild-type T4MO, a 51±9% conversion of benzene was obtained and phenol was produced at a purity of 97%. Relative to the one-phase system, there was a 12-fold reduction in the formation of the byproduct catechol.

Shriniwas D. Samant – One of the best experts on this subject based on the ideXlab platform.

  • ultrasound promoted synthesis of 1 amidoalkyl 2 naphthols via a three component condensation of 2 naphthol ureas amides and aldehydes catalyzed by sulfamic acid under ambient conditions
    Ultrasonics Sonochemistry, 2007
    Co-Authors: Sachin B. Patil, Pankajkumar R. Singh, Mandar P. Surpur, Shriniwas D. Samant

    Abstract:

    Abstract A three-component one-pot condensation of 2-Naphthol, ureas/amides and aldehydes catalyzed by sulfamic acid, under ultrasound irradiation and ambient conditions gives 1-amidoalkyl-2-Naphthols in excellent yield and in short time.

  • Ultrasound-promoted synthesis of 1-amidoalkyl-2-Naphthols via a three-component condensation of 2-Naphthol, ureas/amides, and aldehydes, catalyzed by sulfamic acid under ambient conditions.
    Ultrasonics sonochemistry, 2006
    Co-Authors: Sachin B. Patil, Pankajkumar R. Singh, Mandar P. Surpur, Shriniwas D. Samant

    Abstract:

    A three-component one-pot condensation of 2-Naphthol, ureas/amides and aldehydes catalyzed by sulfamic acid, under ultrasound irradiation and ambient conditions gives 1-amidoalkyl-2-Naphthols in excellent yield and in short time.

Majid Ghashang – One of the best experts on this subject based on the ideXlab platform.

  • Synthesis of a novel series of 7-hydroxy-10-aryl-10H-indeno[1,2-b]chromen-11-ones, indeno[1,2-b]naphtho[1,2-e]pyran-12(13H)-one, and indeno[1,2-b]naphtho[3,2-e]pyran-5,11,13-trione catalyzed by reusable polyvinylpolypyrrolidone-supported triflic acid
    Research on Chemical Intermediates, 2015
    Co-Authors: S. Sheik Mansoor, Majid Ghashang

    Abstract:

    Polyvinylpolypyrrolidone-supported triflic acid (PVPP.OTf) has been used as a recyclable catalyst for synthesis of a series of 7-hydroxy-10-aryl-10H-indeno[1,2-b]chromen-11-one derivatives by condensation of aldehydes, resorcinol, and 2H-indene-1,3-dione. 13-Phenylindeno[1,2-b]naphtho[1,2-e]pyran-12(13H)-one and 12-phenyl-12H-indeno[1,2-b]naphtho[3,2-e]pyran-5,11,13-trione were also synthesized by condensation of benzaldehyde, β-naphthol or 2-hydroxynaphthalene-1,4-dione, and 2H-indene-1,3-dione with PVPP.OTf as catalyst. The heterogeneous catalyst was used for four runs. This method has the advantages of high yields, simple methodology, short reaction times, and easy work-up.

  • Al(HSO_4)_3: an efficient and heterogeneous reusable catalyst for the synthesis of 1-amidoalkyl-2-Naphthols under thermal solvent-free conditions
    Journal of the Iranian Chemical Society, 2012
    Co-Authors: Hamid Reza Shaterian, Majid Ghashang, Manijeh Asadi, Nassrin Tajbakhsh Riki

    Abstract:

    An efficient green protocol for the synthesis of 1-amidoalkyl-2-Naphthols using a three-component, one-pot condensation reaction of 2-Naphthol, aromatic aldehyde and amides in the presence of Al(HSO_4)_3 as heterogeneous catalyst under thermal solvent-free conditions has been described. The present procedure offers advantages such as shorter reaction times, simple work-up procedure, excellent yields, recovery and reusability of catalyst.

  • silica supported perchloric acid hclo4 sio2 an efficient and recyclable heterogeneous catalyst for the one pot synthesis of amidoalkyl naphthols
    Tetrahedron, 2008
    Co-Authors: Hamid Reza Shaterian, Hossein Yarahmadi, Majid Ghashang

    Abstract:

    Abstract An efficient and direct protocol for the preparation of amidoalkyl naphthols employing a multi-component and one-pot condensation reaction of 2-Naphthol, aromatic aldehydes, and acetonitrile or acetamide in the presence of silica supported perchloric acid under solvent, solvent-free, and microwave irradiation conditions is described. The present protocol with HClO 4 –SiO 2 catalyst is superior to the recently reported catalytic methods. It is noteworthy that 1-amidomethyl-2-Naphthols can be converted into important ‘drug like’ 1-aminomethyl-2-Naphthol derivatives by amide hydrolysis.