- Highly selective tetrahydropyranylation/dehydropyranylation of alcohols and phenols using porous phenolsulfonic acid-formaldehyde resin catalyst under solvent-free condition
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An efficient protocol for solvent-free chemoselective tetrahydropyranylation/depyranylation of alcohols and phenols is reported herein using mesoporous Phenolsulfonic Acid Formaldehyde Resins as a heterogeneous acid catalyst. The catalyst successfully performed chemoselective protection and deprotection reactions of a wide range of substrates ranging from primary to secondary and tertiary alcohols and also phenols. The reactions were carried out at ambient temperature under solvent-free condition (SolFC) which resulted in high yields within a very short time. FT-IR, TEM, SEM, EDS and TG-DSC analysis techniques were employed to characterize the synthesized polymeric catalyst. The chemoselective nature of our method was confirmed using 13C DEPT-135 NMR studies. The polymer catalyst was found to be recoverable even after 10th catalytic cycle without much depreciation in its activity. The heterogeneity of the catalyst was verified by hot filtration method. Good yield, energy and cost- effective method, solvent-free protocol, mild reaction conditions, no inert atmosphere, metal-free heterogeneous polymer catalyst and excellent recoverability of the catalyst are notable milestones of the reported protocol.
- Rajkumari, Kalyani,Laskar, Ikbal Bahar,Kumari, Anupama,Kalita, Bandita,Rokhum, Lalthazuala
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- Mild and efficient chemoselective tetrahydropyranylation of alcohols using bronsted acidic ionic liquid as catalyst under solvent-free conditions
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A straightforward and efficient method for preparation of morpholinium bisulfate ([mroH]HSO4) as a novel acidic ionic liquid is reported. The application of this efficient and inexpensive acidic ionic liquid catalyst for tetrahydropyranylation of alcohols under mild and solvent-free conditions at room was investigated.
- Hajipour, Abdol R.,Nasresfahani, Zahra
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experimental part
p. 1995 - 2006
(2012/06/04)
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- Tetrahydropyranylation of alcohols over modified zeolites
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A catalytic amount of Moβ enables tetrahydropyranylation of various alcohols, phenols and naphthols under mild reaction conditions at room temperature in moderate to excellent yields within short reaction times is presented. The catalyst Moβ is reused without significant loss of activity. The product isolation is simple and environmentally benign.
- Narender,Suresh Kumar Reddy,Arun Kumar,Rohitha,Kulkarni
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experimental part
p. 175 - 178
(2010/11/05)
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- Tetrahydropyranylation of alcohols under solvent-free conditions
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A green, efficient, and large-scale method for tetrahydropyranylation of alcohols in the presence of a catalytic amount of pyridinium chloride at room temperature under solvent-free conditions is reported. Copyright Taylor & Francis Group, LLC.
- Hajipour, Abdol R.,Kargosha, Majid,Ruoho, Arnold E.
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experimental part
p. 1084 - 1091
(2009/09/08)
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- Simple and facile tetrahydropyranylation of alcohols by use of catalytic amounts of benzyltriphenylphosphonium tribromide
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An efficient and mild system for protection of a variety of alcohols with 3,4-dihydro-2H-pyran (DHP) in the presence of catalytic amounts of benzyltriphenyl-phosphonium tribromide (BTPTB) (1) gives the corresponding tetrahydropyan ethers (ROTHP) in dichloromethane. The experimental procedure is simple, and the products are straightforwardly isolated in high to excellent yields. Copyright Taylor & Francis, Inc.
- Hajipour,Pourmousavi,Ruoho
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p. 2889 - 2894
(2007/10/03)
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- Stannous chloride dihydrate: A new catalyst for the tetrahydropyranylation of alcohols
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Catalytic Stannous chloride dihydrate in polar aprotic solvents like chloroform efficiently catalyse the tetrahydropyranylation of alcohols in a short time under mild conditions.
- Joju Davis,Bhalerao,Vittal Rao
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p. 1679 - 1686
(2007/10/03)
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- Iodine-Catalyzed Mild and Efficient Tetrahydropyranylation/Depyranylation of Alcohols
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Alcohols and phenols are tetrahydropyranylated rapidly in high yields in the presence of catalytic amount of iodine at room temperature. Depyranylation is effected readily by refluxing with iodine in methanol for few hours.
- Kumar, H. M. Sampath,Reddy, B. V. Subba,Reddy, E. Jagan,Yadav, J. S.
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p. 857 - 858
(2007/10/03)
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- Copper(II)chloride catalyzed tetrahydropyranylation of alcohols
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A simple and efficient methodology for the tetrahydropyranylation of alcohols using catalytic amount of copper(II)chloride in dichloromethane is described. The yields obtained are good to excellent.
- Bhalerao,Davis, K. Joju,Rao, B. Vittal
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p. 3081 - 3085
(2007/10/03)
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- Ceric ammonium nitrate catalysed protection of alcohols by 3,4-dihydro-2H-pyran
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Hydroxyl compounds readily add to dihydropyran in presence of a catalytic amount of ceric ammonium nitrate to give high yield of tetrahydropyranyl ethers.
- Maity,Roy
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p. 1667 - 1671
(2007/10/02)
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