Phenylmethyl ether

In practice the various trityl derivatives are cleaved with acid, but the monomethoxy derivative can be cleaved with sodium naphthalenide in HMPA (90% yield).It is not cleaved by sodium anthracenide, used to cleave a-naphthyldi-phenylmethyl ethers. 

TNAns) Methyl Picrate, or 2,4,6-Trinitro-phenylmethyl Ether, H3C.0.C6H2(N02)3 mw 243.13, N 17.28% yel crysts, d 1.7 1.6 for cast mp 68.4° (pure), 65-67° (coml) Brisance by Cu Cylinder Crusher Test 92% PA or 100% TNT Expln Temp 279° Friction Sensitivity 60 kg (max pressure betw two rubbing surfaces for no expln) Impact Sensitivity with 5-kg wt 19cm Power by Ballistic Mortar 101% PA Rate of Deton 6660m/sec at d 1.59... 

The aromatic, warm, and sweetish odor and taste of the seed, leaves, and stem arises from the presence of a volatile oil that contains anethole p-propenyl phenylmethyl ether, C3H5C6H4OCH3), the derivatives of which (anisole and anisaldehyde) are used in food flavoring, particularly bakery, liqueur, and candy products, as well as ingredients for perfumes. For commercial production of anise oil, the seeds and the dried, ripe fruit of the plant are used. Anise oil. a colorless to pale-yellow, strongly refractive liquid of characteristic odor and taste, is prepared by steam distillation of the seed and fruit. The oil contains choline, which finds use in medicine as a carminative and expectorant. 

Both of these ethers are prepared easily by nucleophilic displacements (Equations 15-7 and 15-8) and can be converted back to the parent alcohol under mild conditions, by catalytic hydrogenation for phenylmethyl ethers (Equation 15-9), or by mild acid hydrolysis for trimethylsilyl ethers (Equation 15-10) ... 

Exercise 15-37 The O-C bond of phenylmethyl ethers is reduced more readily by hydrogen over a metal catalyst than the O-C bond of methyl or ethyl ethers. How do... 

It should be noted that owing to the great affinity of the phenol for sodium, no sodium alcoholate remains to react with the ethyl iodide. Diethyl ether, however, may be prepared in a similar manner, using the same quantities of sodium, alcohol and ethyl iodide as above. The ether and excess of alcohol are distilled off and the ether separated from the alcohol by the addition of salt solution. Anisole (phenylmethyl ether, B.P. 154°, see p. 218) can also be prepared in a similar way, using corresponding quantities of methyl alcohol and methyl iodide. The alkyl iodides give the best yields, but alkyl chlorides can also be employed. 

Kreft, J.-U. and B. Schink. 1993. Demethyation and degradation of phenylmethyl-ethers by the sulfide-methylating homoacetogenic bacterium strain TMBS 4. Arch. Microbiol. 159 308-315. 

Several papers on the transformation of benzene and substituted benzenes to cis-diols using Pseudomonas putida have appeared. A summary on the preparation of cyclitols and natural products such as (+)-pinitol, (+)-conduritol F as well as D-(-)-myo-inositol-1- and l,4,S-tri-phosphate from benzene have been reported. Standard chemical transformations from benzene cu-diol involving resolution of an alcohol intermediate by way of (+)-sec phenylmethyl ethers led to a preparation of (+)-conduritol F and its enantiomei, whereas resolution of an alcohol intermediate using lipase-catalysed acetylation afforded (+)- and (-)-conduritol C. ... 

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