Benzylacetate

Mono- and double carbonylation of phenetyl bromide with cobalt-phosphine catalysts afforded benzylacetic (Baa) and benzylpymvic (Bpa) acids respectively [23] (Scheme 5.5). The highest yield of benzylpymvic acid (75 %) was obtained with [Co2(CO)8], while addition of the water soluble phosphines TPPMS or TPPTS decreased both the yield of carbonylated products and the selectivity to Bpa. 

Carbonylation of phenethyl bromide catalysed by Co2(CO)8 alone or modified either with tppts or tppms yielded products of double- and mono-carbonylation, (benzylpyruvic and benzylacetic acid, respectively) at a concentration of 8 mol% cobalt, 85°C and 20 bar CO under basic conditions in an H20/tBuOH (14/1) solvent mixture (Figure 13).475>476 The reaction rates exhibited by Co2(CO)8 were comparable with the Co2(CO)6(tppts)2 catalyst but replacement of tppts by tppms gave rise to a dramatic decrease in catalytic activity.475 Substantially different double/mono carbonylation (d/m ratios) were observed with Co2(CO)8, Co2(CO)e(tppts)2 and Co2(CO)6(tppms)2 7.3, 2.1 and 0.3, respectively, which... 

Oxidation with peroxydisulfate in AcOH in the presence of catalytic amounts of iron and copper salts gives benzylic acetates in good yields.785,861 The reaction of lead tetraacetate with alkylarenes in AcOH provides benzylacetates in moderate yields.693 Most of these oxidations usually involve methyl-substituted benzenes since aromatics with longer chain produce different side products. 

W C HggH -ICH OOHl Benzylacetic acid, 3-Phenylpropanoic acid OH... 

Toluene was oxidized to a mixture of benzyl acetate (31) and benzylidene diacetate (32) on reaction with oxygen in the presence of a silica supported Pd-Sn catalyst.A reaction run in HOAc/KOAc at 70°C under an atmosphere of oxygen gave a near 3 1 ratio of the monoacetate to the diacetate at 98% conversion (Eqn. 21.40). The two products are formed in parallel reactions as the benzylacetate does not react further under these reaction conditions. Substituted diphenylmethanes were oxidized to the diphenyl ketones by refluxing them in air in a DMF solution containing a copper powder catalyst.""... 

So far, easily available alkyl halides have not been applied to biphasic carbonyla-tions. However, the carbonylation of phenethyl bromide with hydrophilic cobalt catalysts to give benzylpyruvic acid (BPA) and benzylacetic acid (BAA) was investigated (Eq. 11) [21]. 

Beilstein Handbook Reference) AI3-00892 Benzenepropanoic acid Benzeneproplonic acid Benzylacetic acid BRN 0907515 CCRIS 3199 Dihydrocinnamic acid EINECS 207-924-5 FEMA No. 2889 Hydrocinnamic acid NSC 9272 Phenylpropanoic acid 3-Phenylpropanoic acid p-Phenylpropionic acid 3-Phenylpropionic acid. Fixative for perfumes, flavoring. Solid mp = 47-48° bp n 280° Xm = 247, 252, 257, 260, 263, 267 nm (MeOH) soluble in H2O (5.8 g/l), EtOH, Et20, CCl4, CHCI3, CS2, very soluble in CeHe, Greeff R.W. Co. Janssen Chimica Penta Mfg. 

Benzylacetic acid. See Hydrocinnamic acid Benzyl acetoacetate... 

N,N-Dimethyl-4(6 -benzthiazolylazo) aniline N,N-Dimethyl-p-(6-benzthiazolylazo) aniline. See6-Dimethylaminophenylazobenzothiazole 2,4-Dimethyl benzylacetate CAS 62346-96-7 EINECS/ELINCS 263-518-8 Uses Fragrance in cosmetics... 

Synonyms Benzenepropanoic acid Benzenepropionic acid Benzylacetic acid Dihydrocinnamic acid Phenylpropanoic acid 3-Phenylpropanoic acid Phenylpropionic acid 3-Phenylpropionic acid P-Phenylpropionic acid... 

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