- Preparation method of 3,5-dihydroxyamylbenzene
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The invention provides a preparation method of 3,5-dihydroxyamylbenzene. The preparation method comprises the following steps: with a 3,5-dialkoxy benzoate compound as a raw material, subjecting the 3,5-dialkoxy benzoate compound to reacting with valeronitrile to generate a beta-ketone nitrile compound, hydrolyzing a cyano group to generate a carboxylic acid compound, performing a decarboxylation reaction to obtain 3,5-dialkoxyphenylpentanone, performing Huang Ming-long reaction or catalytic hydrogenation to convert 3,5-dialkoxyphenylpentanone into 3,5-dialkoxyamylbenzene, and finally, reducing an alkoxy group into a phenolic hydroxyl group so as to obtain 3,5-dihydroxyamylbenzene. The preparation method provided by the invention overcomes the defects of high cost, complex route, low yield, poor purity and the like of traditional processes.
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- SYNTHESIS AND PURIFICATION OF CANNABIGEROL AND ITS APPLICATION
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The present invention relates to a method for producing cannabigerol and purifying it from a reaction mixture. The present invention also relates to the cosmetic use of cannabigerol for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, in particular for reducing pigmentation of the skin, preferably for the improvement of the appearance of the skin in case of hyperpigmentation, lentigo or vitiligo. Furthermore, the present invention relates to cannabigerol for use in a therapeutic method for the inhibition of tyrosinase activity and/or the reduction of melanin production in the skin, preferably for use in a therapeutic method for the treatment and/or prevention of malign skin disorders, in particular skin cancer.
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Page/Page column 19-20
(2020/12/30)
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- Synthesis method of 3, 5-dihydroxypentene benzene
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The invention provides a synthesis method of 3, 5-dihydroxypentene benzene. The synthesis method comprises the following steps: reacting 3, 5-dimethoxyphenol used as a raw material with a sulfonate halide reagent to generate sulfonate, carrying out cross-coupling reaction with a nucleophilic reagent to introduce amyl, and finally reducing methoxyl into phenolic hydroxyl, thereby obtaining the product 3, 5-dihydroxypentene benzene. The synthesis method solves the defects of high cost, complex route, low yield, poor purity and the like of the traditional process.
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- Synthesis, inhibitory activity and in silico docking of dual COX/5-LOX inhibitors with quinone and resorcinol core
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Based on the significant anti-inflammatory activity of natural quinone primin (5a), series of 1,4-benzoquinones, hydroquinones, and related resorcinols were designed, synthesized, characterized and tested for their ability to inhibit the activity of cyclooxygenase (COX-1 and COX-2) and 5-lipoxygenase (5-LOX) enzymes. Structural modifications resulted in the identification of two compounds 5b (2-methoxy-6-undecyl-1,4-benzoquinone) and 6b (2-methoxy-6-undecyl-1,4-hydroquinone) as potent dual COX/5-LOX inhibitors. The IC50 values evaluated in vitro using enzymatic assay were for compound 5b IC50 = 1.07, 0.57, and 0.34 μM and for compound 6b IC50 = 1.07, 0.55, and 0.28 μM for COX-1, COX-2, and 5-LOX enzyme, respectively. In addition, compound 6d was identified as the most potent 5-LOX inhibitor (IC50 = 0.14 μM; reference inhibitor zileuton IC50 = 0.66 μM) from the tested compounds while its inhibitory potential against COX enzymes (IC50 = 2.65 and 2.71 μM for COX-1 and COX-2, respectively) was comparable with the reference inhibitor ibuprofen (IC50 = 4.50 and 2.46 μM, respectively). The most important structural modification leading to increased inhibitory activity towards both COXs and 5-LOX was the elongation of alkyl chain in position 6 from 5 to 11 carbons. Moreover, the monoacetylation in ortho position of bromo-hydroquinone 13 led to the discovery of potent (IC50 = 0.17 μM) 5-LOX inhibitor 17 (2-bromo-6-methoxy-1,4-benzoquinone) while bromination stabilized the hydroquinone form. Docking analysis revealed the interaction of compounds with Tyr355 and Arg120 in the catalytic site of COX enzymes, while the hydrophobic parts of the molecules filled the hydrophobic substrate channel leading up to Tyr385. In the allosteric catalytic site of 5-LOX, compounds bound to Tyr142 and formed aromatic interactions with Arg138. Taken together, we identified optimal alkyl chain length for dual COX/5-LOX inhibition and investigated other structural modifications influencing COX and 5-LOX inhibitory activity.
- Sisa, Miroslav,Dvorakova, Marcela,Temml, Veronika,Jarosova, Veronika,Vanek, Tomas,Landa, Premysl
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- 3. 5 - Dihydroxy fifth heavenly stem benzene synthetic method
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The invention provides a 3, 5 - dihydroxy fifth heavenly stem benzene synthetic method, through under the acid catalysis of benzene with a Friedel - crafts acylation reaction to obtain the [...], the acid is a Lewis acid; the obtained [...] nitration to obtain 3, 5 - dinitrobenzene pentanone; then into methylene carbonyl reduction after reduction of nitro, to obtain 3, 5 - diamino [...]; diazotisations 3, 5 - diamino [...] variable hydroxy obtain 3, 5 - dihydroxy fifth heavenly stem benzene. The invention raw materials used are cheap and easily obtained bulk chemical raw materials, every one-step reaction conditions are relatively mild, which belongs to the chemical industry a large number of applied to the conventional reaction. In accordance with the technique to obtain the final product 3, 5 - dihydroxy fifth heavenly stem benzene (Olivetol) high purity, can reach 98.5% or more, the single hetero in 0.3% to the inner.
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- Concise access to primin, miconidin and related natural resorcinols
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An efficient and short synthetic procedures affording the biologically active natural products primin, miconidin, olivetol, grevillol, and cardol (adipostatin A) in high yields are reported. The two strategies involve Sonogashira and Suzuki cross-couplings as the crucial steps for the installation of the alkyl side-chains. Syntheses start from cheap, commercially available 1-bromo-3,5-dimethoxybenezene to obtain 1,3-dimethoxy-5-(alk-1-yn-1-yl)benzene as the key intermediate. This intermediate can be easily and economically oxidized to provide primin in excellent overall yield while avoiding undesired side products by the virtue of its symmetry. The demethylation of the key intermediate affords natural resorcinols olivetol, grevillol, and cardol, respectively. The reduction of primin provides its hydroquinone derivative miconidin.
- Sisa, Miroslav,Dvorakova, Marcela,Vanek, Tomas
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p. 5297 - 5301
(2017/08/04)
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- BIOENZYMATIC SYNTHESIS OF THC-v, CBV AND CBN AND THEIR USE AS THERAPEUTIC AGENTS
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The present invention provides methods for producing cannabinoids. More specifically, the invention is directed to the bio-enzymatic synthesis of THC-v, CBV and CBN by contacting a compound according to Formula I with a cannabinoid synthase enzyme. Also described is a system for producing these pharmaceutically important cannabinoids and the use of such cannabinoids as therapeutic agents.
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Paragraph 0122; 0123; 0126; 0127; 0128; 0129
(2017/10/18)
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- BIOSYNTHESIS OF CANNABINOID PRODRUGS AND THEIR USE AS THERAPEUTIC AGENTS
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The present invention provides methods for producing cannabinoid prodrugs. Also described are pharmaceuticals acceptable compositions of the prodrugs and a system for the large-scale production of the prodrugs.
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Paragraph 0189-0192
(2017/11/07)
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- METHODS FOR THE MANUFACTURE OF CANNABINOID PRODRUGS, PHARMACEUTICAL FORMULATIONS AND THEIR USE
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Described are methods for producing cannabinoid prodrugs as well as methods for formulating such prodrugs in a pharmaceutically acceptable form and their use as therapeutic agents for treating diseases.
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Paragraph 0133; 0134; 0135; 0136
(2018/01/18)
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- APPARATUS AND METHODS FOR THE SIMULTANEOUS PRODUCTION OF CANNABINOID COMPOUNDS
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The present invention provides an apparatus and methods for simultaneously producing different compounds in various ratios under set conditions.
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Page/Page column 66; 67
(2016/03/22)
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- BIOSYNTHESIS OF CANNABINOIDS
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The present invention provides methods for producing cannabinoids and cannabinoid analogs as well as a system for producing these compounds. The inventive method is directed to contacting a compound according to Formula I or Formula II with a cannabinoid synthase. Also described is a system for producing cannabinoids and cannabinoid analogs by contacting a THCA synthase with a cannabinoid precursor and modifying at least one property of the reaction mixture to influence the quantity formed of a first cannabinoid relative to the quantity formed of a second cannabinoid.
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Paragraph 0120-0122
(2014/09/16)
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- Two Novel Alkylresorcinol Synthase Genes from Sorghum; Cloning, Expression, Transformation and Characterization
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Sorghum is considered to be an allelopathic crop species, producing phytotoxins such as the lipid benzoquinone sorgoleone (2-hydroxy-5-methoxy-3-[(Z,Z)-8′,11′,14′-pentadecatriene]-p-benzoquinone) which likely accounts for much of its allelopathic properties. Prior investigations into the biosynthesis of sorgoleone have suggested the participation of one or more alkylresorcinol synthases (ARS), which are type III polyketide synthases (PKS) that produce 5-alkylresorcinols using medium to long-chain fatty acyl-CoA starter units via iterative condensations with malonyl-CoA. Current evidence suggests that sorgoleone biosynthesis occurs exclusively in root hair cells, involving the synthesis of a 5-pentadecatrienyl resorcinol intermediate derived from an unusual 16:3 fatty acyl-CoA starter unit. To characterize the enzymes responsible for the biosynthesis of this alkylresorcinol intermediate, a previously-described expressed sequence tag (EST) database prepared from isolated root hairs was first mined for all PKS-like sequences. Quantitative real-time RT-PCR analyses revealed that two of these sequences were preferentially expressed in root hairs, and recombinant enzyme studies demonstrated that both sequences (designated ARS1 and ARS2) encode ARS enzymes capable of accepting a variety of fatty acyl-CoA starter units. Furthermore, RNA interference (RNAi) experiments directed against ARS1 and ARS2 resulted in the generation of multiple independent transformant events exhibiting dramatically reduced sorgoleone levels. Thus, both ARS1 and ARS2 are likely to participate in the biosynthesis of sorgoleone in planta. The sequences of ARS1 and ARS2 were also used to identify several rice genes encoding ARSs, which are likely involved in the production of defense-related alkylresorcinols.
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- Ultrasound-assisted Wittig reaction and synthesis of 5-alkyl- and 5-alkenyl-resorcinols
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Some 5-alkyl- and 5-alkenyl-resorcinols were synthesised from commercially available 3,5-bis(benzylo×y)benzaldehyde by ultrasound-assisted Wittig reaction with alkyltriphenyl phosphonium bromides in basic aqueous condition, followed by debenzylation and simultaneously reduction of a double bond of the styrene type with Na/n-BuOH in overall yields of 62-72%.
- Wu, Li-Qiang,Yang, Chun-Guang,Yang, Li-Ming,Yang, Li-Juan
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experimental part
p. 183 - 185
(2009/11/30)
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- Scope and limitations of lithium-ethylenediamine-THF-mediated cleavage at the α-position of aromatics: Deprotection of aryl methyl ethers and benzyl ethers under mild conditions
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The scope and limitation of lithium-ethylenediamine-THF-mediated reductive bond cleavage at the α-position of aromatics were examined. Very mild conditions such as lithium metal (5 equiv) and ethylenediamine (7 equiv) in oxygen-free THF were quite effective for the demethylation of aromatic ethers even at as low as -10°C. Allyl benzyl ethers were also deprotected under these conditions with very little change of the allylic alcohol moiety. Through this study, 2,6-dimethylbenzyl (m-xylylmethyl, MXM) group was developed as an alternative of benzyl group, which is readily cleavable under the above mentioned reductive conditions.
- Shindo, Takeyuki,Fukuyama, Yasuaki,Sugai, Takeshi
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p. 692 - 700
(2007/10/03)
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- Simple synthesis of 5-substituted resorcinols: A revisited family of interesting bioactive molecules
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The reaction of 3,5-dimethoxybenzyl trimethylsilyl ether (3) with different aldehydes (n-PrCHO, n-C11H23CHO, MeCHO, PhCHO) in the presence of lithium powder and a catalytic amount of naphthalene (4 mol %) gave, after hydrolysis, the expected alcohols 4 in moderate yields. The dehydroxylation of these compounds through the corresponding mesylates 5 or directly from benzylic derivatives by catalytic hydrogenation, afforded compounds 6, which are finally demethylated to yield 5-alkyl-3,5-dihydroxyresorcinols, such as olivetol (7a), grevillol (7b), 1,3-dihydroxy-5-propylbenzene (7c), or dihydropinosilvine (7d). Dehydration of alcohol derivatives 4 followed by demethylation led to hydroxylated stilbene-type structures, such as pinosilvine (9d), resveratrol (9e), or piceatannol (9f), which in some cases can be hydrogenated to give saturated molecules such as combretastanin B-4 tetramethyl ether (6f) or chrysotobibenzyl (6g). Finally, when the naphthalene-catalyzed lithiation of compound 3 was performed in the presence of other electrophiles [Me3SiCl, t-BuCHO, CH3(CH2)4CHO, 4-Me3SiOC6H4CHO, (CH2)5CO, PhN = C = O, PhN = CHPh], the expected reaction products 12 were isolated, after hydrolysis.
- Alonso, Emma,Ramon, Diego J.,Yus, Miguel
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p. 417 - 421
(2007/10/03)
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- Synthesis of 11-nor-Δ-9-tetrahydrocannabinol-9-carboxylic acid glucuronide
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A method of producing a deuterated or undeuterated 11-nor-Δ8 -tetrahydrocannabinol (THC) glucuronide or deuterated or undeuterated 11-nor-Δ9 -THC glucuronide by reacting a blocked THC carboxylic acid precursor with a blocked sugar epoxide precursor is disclosed. Also disclosed are: deuterated 11-nor-Δ8 - or Δ9 -THC carboxylic acid glucuronide having a deuterated hydrocarbon chain; 5'-deuterated 11-nor-Δ8 - or Δ9 -THC-carboxylic acid or 5'-deuterated Δ8 - or Δ9 -THC glucuronide. The compositions are useful as GC-MS standards; in methods for preparing antibodies reactive with a THC glucuronide; and, in GC-MS diagnostic methods for THC metabolites.
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- A convenient, practical synthesis of substituted resorcinols: Synthesis of DB-2073 and olivetol
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A wide variety of easily accesible 1,3-cyclohexanediones are readily transformed to substituted dimethyl resorcinols with iodine and methanol.
- Kotnis, Atul S.
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p. 3441 - 3444
(2007/10/02)
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- Thermal Decomposition of Lichen Depsides
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The thermal decomposition of the following lichen depsides has been described: lecanoric acid, gyrophoric acid, evernic acid, perlatolic acid, planaic acid, confluentic acid, atranorin, 4-O-demethylbarbatic acid, and sekikaic acid.Main reaction products are decarboxylated compounds, phenolic units, rearranged depsides, and xanthones.Triethylammonium salts of depside carboxylic acids decompose at reasonably lower temperature than the corresponding free acids. - Keywords: Lichen Depsides, Thermal Decomposition
- Huneck, Siegfried,Schmidt, Juergen,Tabacchi, Raffaele
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p. 1283 - 1289
(2007/10/02)
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- BIOLOGICALLY ACTIVE PHENOLIC METABOLITES OF A VERTICICLADIELLA SPECIES
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The metabolites produced when a Verticicladiella species (Canadian Forestry Service strain C728), the causative agent of the black stain root disease of many conifers, is grown in liquid culture have been investigated.Orcinol, orcinol monomethyl ether, 1,3,6,8-tetrahydroxyanthraquinone, and the α-L-rhamnopyranosides of orcinol and orcinol methyl ether have been isolated and indentified.Orcinol methyl ether and its rhamnoside both show antibacterial activity and orcinol methyl ether also inhibits the growth of pine germlings.The general antibacterial activity of 5-alkylresorcinols and their monomethyl ethers is reported.-Key Word Index-Verticicladiella sp.; Deuteromycontina; blue-stain fungus; phytotoxin; phenols; methylorcinol rhamnoside; phenol monomethyl ethers; antiseptics.
- Ayer, William A.,Browne, Lois M.,Lovell, Sarah H.
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p. 2267 - 2272
(2007/10/02)
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- A BIOMIMETIC SYNTHESIS OF 1Δ-TETRAHYDROCANNABIOL
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Condensation of 1,3-bis(trimethylsiloxy)-1-methoxybutadiene with the acid chloride 12 gave methyl olivetolate (13).Condensation of 13 with (+)-p-mentha-2,8-dien-1-ol gave methyl 1Δ-tetrahydrocannabiolate (14) in 55percent isolated yield.Alkaline hydrolysis of 14 gave 1Δ-tetrahydrocannabinol (1, 1Δ-THC).The synthesis is patterned after the biogenesis of 1.
- Chan, T. H.,Chaly, T.
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p. 2935 - 2938
(2007/10/02)
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- Long-chain Phenols. Part 16. A Novel Synthesis of Homologous Orsellinic Acids and their Methyl Ethers
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By the novel reaction of 3,5-dimethoxyfluorobenzene with n-alkyl-lithium compounds, followed by carbonation, homologous orsellinic acid dimethyl ethers (6-alkyl-2,4-dimethoxybenzoic acids) have been obtained.The reactions proceeded best with the homologues of methyl-lithium.These reactions are considered to occur by way of 3,5-dimethoxybenzyne. 2,4-Dimethoxyfluorobenzene did not form an aryne but gave 3-fluoro-2,6-dimethoxybenzoic acid instead.Decomposition with water of alkyl-lithium reaction mixtures from 3,5-dimethoxyfluorobenzene yielded 5-n-alkylresorcinol dimethyl ethers.Demethylaton of 6-alkyl-2,4-dimethoxybenzoic acids with boron trichloride proceeded partially and selectively to give the 6-alkyl-2-hydroxy-4-methoxybenzoic acids, and completely with aluminium chloride to give the homologous orsellinic acids.Boron tribromide was less effective, but readily gave the 5-alkyl resorcinols from the corresponding dimethyl ethers.
- Durrani, Aziz A.,Tyman, John H. P.
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p. 1658 - 1666
(2007/10/02)
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- A New Route to 5-Substituted Resorcinols and Related Systems
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Michael-type additions of phenylsulphinylacetate esters to αβ-unsaturated ketones produce cyclohexane-1,3-dione derivatives, which, after thermal elimination of benzenesulphenic acid, give the corresponding 5-substituted resorcinols, such as olivetol.The scope of this entry into other aromatic systems, such as 3,5-disubstituted and 2,3,5-trisubstituted phenols and orsellinic acid has been explored.
- Jaxa-Chamiec, Albert A.,Sammes, Peter G.,Kennewell, Peter D.
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p. 170 - 175
(2007/10/02)
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- Course of Aromatisation of 5-Alkyl/aryl-2-bromocyclohex-2-en-3-ol-1-ones to Corresponding 5-Alkyl/arylresorcinols
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5-Alkyl/aryl-2-bromocyclohex-2-en-3-ol-1-ones on heating undergo aromatisation through dehydrobromination to the corresponding 5-substituted resorcinols.During the course of aromatisation of 2-bromo-5-methylcyclohex-2-en-3-ol-1-one (I) and 5-n-amyl-2-bromocyclohex-2-en-3-ol-1-one (II) a few intermediates have been isolated and characterised as IV, V, VI, VIII and IX.Similar studies on 2-bromo-5-phenylcyclohex-2-en-3-ol-1-one yields two structurally different products, one with no bromine (XI) and the other with bromine in position-2 (XII), besides 5-phenylresorcinol (XIII).
- Chandrasekharan, V.,Unnikrishnan, P.,Shah, G. D.,Bhattacharyya, S. C.
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p. 1052 - 1055
(2007/10/02)
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- Process for the preparation of 5-substituted resorcinols and related intermediates
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According to the present invention, 5-substituted resorcinols of the formula I STR1 wherein R1 represents a hydrocarbon radical, optionally unsubstituted or substituted by inert substituents, are prepared by reacting a carboxylic acid ester of the formula II wherein R2 represents a non-aromatically bound lower hydrocarbon radical, in the presence of an alkaline condensation agent, with a diester of 3-oxoglutaric acid of the formula III wherein R3 and R4 represent non-aromatically bound lower hydrocarbon radicals; hydrolyzing the resulting dihydroxyisophthalic acid acid ester of the formula IV STR2 and decarboxylating the hydrolyzed product, a specific embodiment is the preparation of 5-pentylresorcinol.
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