Hydroxy benzyl alcohol

NX - BENZYL ALCOHOL, -HYDROXY-alpha-( (METHYLAMINO)METHYL >-, HYDROCHLORIDE, (-)-... 

The acid hydrolysis product was identified, as 2-propanyI-4,5-methylene-dioxy benzyl alcohol (hydroxy me thy Id ihydrosafrolc or HMDS), with the structure shown below ... 

Cholesterol Cortisol Testosterone Bile salts PAHs (benzylic alcohols) Hydroxy-tamoxifen Ala261Thr... 

Dimethoxybenzyl esters prepared from the acid chloride and the benzyl alcohol are readily cleaved oxidatively by DDQ (CH2CI2, H2O, rt, 18 h, 90-95% yield). A 4-methoxybenzyl ester was found not to be cleaved by DDQ. The authors have also explored the oxidative cleavage (ceric ammonium nitrate, CH3CN, H2O, 0°, 4 h, 65-97% yield) of a variety of 4-hydroxy- and 4-amino-substituted phenolic esters. ... 

The use of benzyl alcohol as solvent produces the dibenzyl acetal at C-21, and this can be reductively removed to produce the 21-hydroxy compound... 

Recently, it was found that the addition of benzylamine to 2-(5//)-furano-3-ylmethanesulfonate 280 (X = O—SOaMe) in methanol afforded a 7 1 mixture of the trans- and cw-methyl-A-benzyl-2-hydroxymethylaziridine-2-carboxylates 281 and 282, respectively (00TL3061). Treatment of 281 with benzyl alcohol in the presence of BF3 OEta furnished, after hydrolysis, rac-cw-amino-a-hydroxy-/3-butyrolactone 284 (Scheme 74). 

Chemical Name 4-hydroxy-3,5-diiodo-0 -[1-[(1-methyl-3-phenylpropyl)amino] ethyl] benzyl alcohol... 

Chemical Name 3,5-dihydroxy-0 -[ [(p-hydroxy-a -methylphenethyl)amino] methyl] benzyl alcohol hydrobromide... 

As previously described, die main intermediates generated from die initial reaction between ortho reactive sites on novolac resins and HMTA are hydroxy-benzylamines and benzoxazines.44 Triazines, diamines, and, in die presence of trace amounts of water, benzyl alcohols and ethers also form (Fig. 7.16). Similar intermediates, with the exception of benzoxazines, are also observed when para sites react with HMTA. 

Figure 33. Catalytic activity for the oxidation of hydroxy benzyl alcohol with O2 as a function of mean particle diameter of Pd and Au [102].

The availability of Nafion on silica has not only lowered the cost of the resin but also has made it versatile (Sun et al., 1997 Harmer et al., 1998). A number of industrially important reactions have been attempted, with considerable success, with these catalysts. Consider the Fries rearrangement of phenyl acetate to p-acetyl phenol (/t-hydroxy acetophenone). This has been accomplished by Hoelderich and co-workers (Heidekum, 1998). In the ca.se of alkylation of benzene with benzyl alcohol, Amberlyst-15 and p-toluene sulphonic acid are ineffective and Nafion on silica works well at 80 °C. 

The preservatives I select for my formulations is much more limited than the ten listed in the above reference. The products which I develop for a company with natural ingredients image, restricted me to the para hydroxy benzoic acids, benzyl alcohol and phenoxyethanol. I have been allowed to use Myavert C during the last two years due to increase in customer complaints which was assumed to be due to the high levels of phenoxyethanol and benzyl alcohol used hence allergic reaction to the... 

In order to prepare multi-kilogram quantities of 1 our efforts were strictly focused on the development of an asymmetric route. Our retrosynthetic approach was centered on the preparation of cyclopentenone 27 which, we envisioned, could be elaborated to chiral hydroxy acid 26 through a series of asymmetric transformations (Scheme 7.4). Etherification of the hydroxy group of 26 with benzylic alcohol 25 followed by installation of (P)-nipecotate 23 at the acid position of 24, would furnish the drug candidate 1. This section will address the following ... 

Highly diasteroselective and chemoselective reductions may be performed on the hydroxy functions of (r/6-arene)-tricarbonylchromium complexes. Treatment of the chromium-complexed benzylic alcohol 29 with triethylsilane and boron trifluoride etherate in dichloromethane at —78° to 0° gives only diastereomer 30 in 75% yield (Eq. 40).181 In a similar fashion, treatment of the complexed exo-allyl-endo-benzylic alcohol 31 with an excess of Et3SiH/TFA in dichloromethane at room temperature under nitrogen produces only the endo-aflyl product 32 in 92% yield after 1.5 hours (Eq. 41). It is noteworthy that no reduction of the isolated double bond occurs.182... 

Benzophenone, conversion to ethyl /S-hydroxy-0,0-diphenylpro-pionate, 44, 57 Benzophenone oxime, 44, 52 Benzopyrazole, 42, 69 3-Benzoylpropionic add, condensation with benzaldehyde to give a-benzylidene-y-phenyl-A y -bu-tenolide, 43, 3 N-Benzylacetamide, 42,18 n-Benzyiacrylamide, 42,16 Benzyl alcohol, reaction with acrylonitrile, 42,16... 

DMI) for the condensation of the m-hydroxy-benzyl alcohol (15) with chlorobenzene. 

A variant that eliminates the production of water and that has proved effective for esterification of hydroxy and aromatic amino acids involves the use of thionyl chloride instead of acid. At a low temperature, the alcohol reacts with the chloride, generating methyl sulfinyl chloride, which produces the ester, probably through the mixed carboxylic acid-sulfinic acid anhydride (Figure 3.18, B). p-Toluenesulfonyl chloride added to the acid and benzyl alcohol serves the same purpose in the preparation of benzyl esters. 

Benzyloxy-2-methylpropane-l,2-diol, a desymmetrized form of 2-methylpropane-1,2,3-triol with its terminal hydroxy being protected as a benzyl ether, was prepared using the B. subtilis epoxide hydrolase-catalyzed enantioselective hydrolysis of the racemic benzyloxymethyl-l-methyloxirane readily available from methallyl chloride and benzyl alcohol. The preparation of the racemic epoxide, a key intermediate, was described in Procedures 1 and 2 (Sections 5.6.1 and 5.6.2), its overall yield being 78 %. The combined yield of enantiomerically pure (7 )-3-benzyloxy-2-methylpropane-l,2-diol was 74 % from ( )-benzyloxymethyl-l-methyloxirane, as described in Procedures 3-5 (Sections 5.6.3 and 5.6.5), with the overall procedures leading to the biocatalytic dihydroxylation of benzyl methallyl ether . 

Oxidation of benzyl alcohol catalysed by chloroperoxidase exhibits a very high prochiral selectivity involving only the cleavage of the pro-S C-H bond. The reaction mechanism involved the transfer of a hydrogen atom to the ferryl oxygen of the iron-oxo complex. An a-hydroxy-carbon radical and the iron-hydroxy complex P-Fe -OH form. They may lead to the hydrated benzaldehyde or stepwise with the formation of the intermediate a-hydroxy cation. 

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