4- Hydroxy-3-methoxy-benzyl alcohol

A recent method to introduce a carboxyl group ortlw to hydroxy methyl group may be mentioned here. This involves thallation of a benzyl alcohol The reaction is governed by orientation rules observed for acid catalysed electrophilic substitution reaction. Thus m-methoxy benzyl alcohol gives 5-methoxy phthalide... 

One of the side reactions gives the corresponding benzyl alcohol (and its oxidation product, the aldehyde). Related to these reactions is the anodic hydroxylation of 1-carbo-methoxy-l,2,3,4-tetrahydrocarbazoles to the corresponding 1-hydroxy-1-carbomethoxy-1,2,3,4-tetrahydrocarbazoles in MeCN-H20 mixtures [24]. 

Benzeneethanol, 4-hydroxy-3-methoxy-Benzeneethanol, 4-methyl-Benzenemethanol (benzyl alcohol ... 

Preparation by adding 2-hydroxy-3-iodo-6-methoxy-acetophenone and cuprous iodide to a solution of sodium benzylate, previously prepared from benzyl alcohol and sodium hydride in DMF [2524],... 

The oxirane ring in 175 is a valuable function because it provides a means for the introduction of the -disposed C-39 methoxy group of rapamycin. Indeed, addition of CSA (0.2 equivalents) to a solution of epoxy benzyl ether 175 in methanol brings about a completely regioselective and stereospecific solvolysis of the oxirane ring, furnishing the desired hydroxy methyl ether 200 in 90 % yield. After protection of the newly formed C-40 hydroxyl in the form of a tert-butyldimethylsilyl (TBS) ether, hydrogenolysis of the benzyl ether provides alcohol 201 in 89 % overall yield. 

No new TV-benzyltetrahydroisoquinolines have been isolated from natural sources in recent years. However, the structure of corgoine has been confirmed by three syntheses. The first involves reduction of the 7V-benzyl quaternary salt derived from isoquinoline 1, whereas the second approach utilizes the Pictet-Spengler reaction to cyclize the substituted phenethylamine 2 (see Scheme 31.1). The third synthesis of corgoine involves heating 6-methoxy-7-hydroxy-tetrahydroisoquinoline with / -hydroxybenzyl alcohol to afford the alkaloid in 44% yield. The A -benzylation probably occurs through the intermediacy of /7-benzoquinone methide which adds to the basic nitrogen of the isoquinoline. ... 

Also obtained by saponification of 6-hydroxy-2,4-di-methoxy-3-(phenylacetoxy) phenyl benzyl ketone with 10% alcoholic potassium hydroxide for 2 h on a water bath [5387]. 

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