N-Butyl phenylacetate

PHENYLACETATE n-BUTYL PHENYLACETATE PHENYLETHANOIC ACID BUTYL ESTER... 

Successful results have been obtained (Renfrew and Chaney, 1946) with ethyl formate methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, sec.-butyl and iso-amyl acetat ethyleneglycol diacetate ethyl monochloro- and trichloro-acetates methyl, n-propyl, n-octyl and n-dodecyl propionates ethyl butyrate n-butyl and n-amyl valerates ethyl laurate ethyl lactate ethyl acetoacetate diethyl carbonate dimethyl and diethyl oxalates diethyl malonate diethyl adipate di-n-butyl tartrate ethyl phenylacetate methyl and ethyl benzoates methyl and ethyl salicylates diethyl and di-n-butyl phthalates. The method fails for vinyl acetate, ieri.-butyl acetate, n-octadecyl propionate, ethyl and >i-butyl stearate, phenyl, benzyl- and guaicol-acetate, methyl and ethyl cinnamate, diethyl sulphate and ethyl p-aminobenzoate. 

This product is sufficiently pure for the preparation of phenylacetic acid and its ethyl ester, but it contains some benzyl tso-cyanide and usually develops an appreciable colour on standing. The following procedure removes the iso-cyanide and gives a stable water-white compound. Shake the once-distilled benzyl cyanide vigorously for 5 minutes with an equal volume of warm (60°) 60 per cent, sulphuric acid (prepared by adding 55 ml. of concentrated sulphuric acid to 100 ml. of water). Separate the benzyl cyanide, wash it with an equal volume of sa+urated sodium bicarbonate solution and then with an equal volume of half-saturated sodium chloride solution- Dry with anhydrous magnesium sulphate and distil under reduced pressure. The loss in washing is very small (compare n-Butyl Cyanide, Section 111,113, in which concentrated hydrochloric acid is employed). 

With the same procedure /-butyl phenylacetate has been prepared in 47% yield.4 When esters of less common alcohols were prepared, anhydrous ether was used as a solvent instead of excess alcohol. Equivalent amounts of alcohol, n-butyllithium, and acid chloride were employed. Thus the triethylcarbinol ester of p-toluic acid and the 2,2-diphenylethanol ester of benzoic acid have been prepared in 72 and 70% yields, respectively. 

Figure 3.4.10 Intra-molecularly coordinated tri-n-butyl- and triphenyl-tin benzoates, phenylacetates, and cinnamates investigated in order to correlate the potentiometric chloride response with the Lewis acidity of the organotin carrier...

Butyl isooctadecanoate. See Butyl isostearate n-Butyl isopentanoate. See n-Butyl isovalerate Butyl isophenyl acetate. Seejsobutyl phenylacetate... 

Butyl lactate Butyl laurate Butyl levulinate N-Butyl-2-methylbutyrate Butylparaben Butyl phenylacetate n-Butyl propionate Butyl salicylate Butyl stearate Butyl sulfide Butyl 10-undecenoate Butyl valerate n-Butyraldehyde n-Butyric acid Cadinene Camphene Caproic acid Caprylic alcohol Carvacrol Carvacryl ethyl ether Carveol 4-Carvomenthenol Carvone d-Carvone cis-Carvone oxide... 

Benzyl acetate Benzyl propionate Bergamot (Citrus aurantium bergamia) oil y-Bisabolene Bitter almond (Prunus amygdalus amara) oil DL-Borneol Bornyl acetate L-Bornyl acetate Buchu leaves oil 3-Butylidenephthalide Butyl-(S)-lactate Butyl phenylacetate n-Butyl propionate 3-Cadinene 2-Carenyl methyl ketone... 

For the N-terminal deprotection of peptides, the enzyme penicillin G acylase from E. coli has been applied. This attacks phenylacetic acid (PhAc) amides and esters but does not hydrolyze peptide bonds [12-14,25]. The danger of a competitive cleavage of the peptide backbone at an undesired site, which always exists when proteases like trypsin and chymotrypsin are used, is overcome by using the acylase. The penicillin G acylase accepts a broad range of protected dipeptides (27) as substrates, and selectively liberates the N-terminal amino group under almost neutral conditions (pH 7-8, room temperature), leaving the peptide bonds as well as the C-terminal methyl-, allyl-, benzyl-, and tert-butyl ester unaffected (Fig. 8) [25a,bj. On the other hand, the phenylacetamide... 

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