Preparation phenols

Wexler MR, Halon DA, Teitelbaum A, et al (1984) The prevention of cardiac arrhythmias produced in an animal model by topical application of a phenol preparation in common use for face peeling. Plast Recontsr Surg 73 595-598... 

EPA. 1980. Ambient water quality criteria document for phenol. Prepared by the U.S. Environmental Protection Agency, Office of Health and Environmental Assessment, Environmental Criteria and Assessment Office, Cincinnati, OH for the Office of Water Regulations and Standards, Washington, DC. EPA 440/5-80-001A. NTIS PB81-117772. 

Problem 19.33 From phenol prepare (a) p-benzoquinone, (b) p-benzoquinone dioxime, (c) quinhydrone (a 1 1 complex of p-benzoquinone and hydroquinone). 4... 

Chemists from Merck [25] have also described the use of the Mitsunobu reaction for the functionalization of either phenols or benzyl alcohols using TMAD/Bu3P. Similar chemistry has been applied successfully to intermediate phenols prepared using the Mimo-tope pin technology [26],... 

Jensen KJ, Meldal M, Bock K, Glycosilation of phenols preparation of 1,2- cis and 1,2- trans glycosylated tyrosine derivatives to be used in solid-phase glycopeptide synthesis, J. Chem. Soc. Perkin. Trans., 1, 2119, 1993. 

For extracting total DNA from large amounts of plant tissue, use the above procedure, omitting the sucrose gradients (i.e., do Steps 1-6 and 10-15). After the 2-propanol extraction and dialysis for 2 hr or longer, use an equal volume of Tris-buffered phenol [prepared just before use by adding 1/10 volume of unbuffered Tris to 1 volume of water-saturated phenol (IBI, New Haven, CT)] to extract DNA twice, followed by an ether extraction. The DNA is then dialyzed as above. 

Bozell, J. J., Hames, B. R., and Dimmel, D. R., Cobalt-Schiff base complex-catalyzed oxidation of parasubsti-tuted phenolics - Preparation of benzoquinones. J Organic Chem 1995, 60 (8), 2398-2404. 

B. H-(2,4-Diformyl-S-hydroxyphenyl)acet amide. A suspension of 95 g of the phenol (prepared under Section A) (Note 6) in 1 L of aqueous 10% hydrochloric acid is stirred for 2 hr at room temperature. The colorless solid (Note 7) is filtered by suction and twice suspended in water at 40°C. Final filtration is followed with a water wash (1 L, 40°C), and the solid is sucked down on the filter. Crystallization from 800 mL of acetonitrile affords 21.8-22.3 g (66-67.5%) of TV-(2,4-diformyl-5-hydroxyphenyl)acetamide, mp 215-217°C (Note 8). 

Angular Rotation Determine as directed under Optical (Specific) Rotation, Appendix IIB, using a 100-mm tube. Phenols Prepare a 1 3 solution of recently distilled sample in 90% alcohol. It is neutral to moistened litmus paper, and adding 1 drop of ferric chloride TS to 5 mL of the solution produces no blue or brown color. 

In the laboratory, simple phenols can be prepared from aromatic sulforae acids by melting with NaOH at high temperature (Section 16-2), Few functional groups can survive such harsh conditions, though, and the reaction is therefore limited to the preparation of alkyl-substituted phenols. Well see a better method of phenol preparation from aromatic amines in Section 24.8. 

With the exception of 4-(1,1,3,3-tetramethylbutyl)phenol prepared from diisobutylene, all the mutti-branched alkylphenols discussed consist of isomeric mixtures. In the pursuance of structure/property interests several studies have aimed to synthesise pure compounds. Thus by Wurtz-type methodology the reaction of the isomeric chloroanisoles with (i) alkyl iodides in ethereal solution in the presene of sodium and (ii) demethylation of the resultant alkylanisoles with aluminium bromide, a range of C5, Cg and Cg alkylanisoles has been synthesised (ref. 14). Numerous other methods are available for the synthesis of the isomeric n-, iso-, sec- and tert-alkylphenols some of which are referred to in Chapter 13. Reaction of a mixture of the appropriate alkyl chloride and 2-,... 

Sulfonates and sulfates find use as intenpediates for preparing organic compounds not containing sulfur, notably phenols (prepared by caustic fusion of various sulfonates) and alcohols (made by hydrolysis of sulfated... 

Synthetic applications of tetrazoles are deoxygenation of phenols, preparation of nitrilimines and preparation of 1,3,4-oxadiazoles by the Huisgen reaction. All these have been previously... 

Bozell JJ, Hames BR, Dimmel DR (1995) Cobalt-Schiff base complex-catalyzed oxidation of ptira-substituted phenolics - preparation of benzoquinones. J Org Chem 60 2398... 

Xue, H.G., and Z.Q. Shen. 2002. A highly stable biosensor for phenols prepared by immobilizing polyphenol oxidase into polyanfline-polyacrylonitrile composite matrix. Talanta 57 (2) 289. 

This variation of the Sandmeyer reaction (developed by T. Cohen, University of Pittsburgh) is a much simpler and safer procedure than an older method for phenol preparation, which required heating the diazonium salt with concentrated aqueous acid. 

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