A Phenylethyl alcohol

An oxirane process utilizes ethylbenzene to make the hydroperoxide, which then is used to make propylene oxide [75-56-9]. The hydroperoxide-producing reaction is similar to the first step of cumene LPO except that it is slower (2,224,316—318). In the epoxidation step, a-phenylethyl alcohol [98-85-1] is the coproduct. It is dehydrated to styrene [100-42-5]. The reported 1992 capacity for styrene by this route was 0.59 X 10 t/yr (319). The corresponding propylene oxide capacity is ca 0.33 x 10 t/yr. The total propylene oxide capacity based on hydroperoxide oxidation of propylene [115-07-1] (coproducts are /-butyl alcohol and styrene) is 1.05 x 10 t/yr (225). 

The coproduct a-phenylethyl alcohol could be dehydrated to styrene. 

CL-Phenylethanol (a-Phenylethyl alcohol, Methyl-phenyl carbinol). C6H5, CHOH.CH3, mw 122.16, liq, bp 203.6° at 475mm, d 1.019g/cc at 13/4°. Prepn and other properties are given in Beil 6,475, (236) [445]... 

Probitm 16.95 Reaction of the (R)-tosyl ester of a-phenylethyl alcohol (C H,CHMeOTs) with CH,COOH yields a mixture of (S)- and rac-acetate. Explain. 

Alkene oxides may also be cleaved by reduction with lithium aluminum hydride as in the preparation of a-phenylethyl alcohol from styrene oxide (9 4%). ... 

Zeolite-encapsulated perfluorinated ruthenium phthalocyanines catalyze the oxidation of cyclohexane with t-BuOOH [146]. A dioxoruthenium complex with a D4-chiral porphyrin ligand has been used for the enantioselective hydroxylation of ethylbenzene to give a-phenylethyl alcohol with 72% e.e. [147]. 

A mixture of 10 g. (0.082 mole) of a-phenylethyl alcohol and 75 g. of constant-boiling aqueous hydrochloric acid (sp. gr. 1.10) is shaken vigorously at room temperature for about 10 minutes. The organic... 

In 93 per cent yield by heating a-phenylethyl alcohol with 5 per cent of sodium or potassium bisulfite, Gauthier and Gauthier, Bull. soc. chim. [4I 53,323 (1933). 

Problem 12.2 How might you prepare 2,3-diphenyIbutane from a-phenylethyl alcohol, C6H5CHOHCH3 ... 

In principle it should be also possible to synthesise a dihydroisocoumarin by lithiation of a phenylethyl alcohol. Such a synthesis however is not reported. Phenylethyl... 

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