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Benzyl cyanide hydrolysis to acid
Hydrolysis of benzyl cyanide to phenylacetic
acid. Into a 500 ml. round-bottomed ;lask,
provided with a re;lux condenser, place 100
ml. [Pg.761]
Hydrolysis of a nitrile to an amide. Warm a
solution of 1 g. of the nitrile benzyl cyanide)
in 4 ml. of concentrated sulphuric acid to 80-
90°, and allow the solution to stand for 5
minutes. Cool and pour the solution
cautiously into 40 ml. of cold water. Filter
o;lT the precipitate stir it with 20 ml. of cold
5 per cent, sodium hydroxide solution and
;ilter again. RecrystaUise the amide from
dilute alcohol, and determine its m.p.
Examine the solubility behaviour and also the
action of warm sodium hydroxide solution
upon the amide. [Pg.1077]
Dilute sulfuric acid is used for hydrolysis of
phenylacetonitrile (benzyl cyanide) to
phenylacetic acid 626 [Pg.351]
The common route to phenylacetic acid is
conversion of benzyl chloride into benzyl
cyanide by reaction with sodium cyanide,
followed by hydrolysis. [Pg.119]
Benzylamine, 394, 560, 569 Benzylaniline.
572 Benzyl chloride, 517, 534, 538, 539
Benzyl cyanide, 752, 761 hydrolysis to acid,
761 hydrolysis to phenylacetamide, 762
Benzylidene derivatives, 345, 653 Benzyl
magnesium chloride, 517 Benzyl
phthalimide, 560, 569 Benzyl-sodium, 933 -
Benzyl-iso-thiuronium cliloride, 965,
966 [Pg.1169]
Fig. 11.12.
Metabolic
scheme for
reaction of
benzyl cyanide
(11.80) to
mandelonitrile
(11.81) as a
crossroads to
benzoic acid
(11.83) via
oxidative
denitrilation,
and to
mandelic acid
(11.82) as a
minor
metabolite
produced by
hydrolysis of
the CN group
[118][122]
Another method of preparing ,to-diarylated
alkanoic acids utilizes the condensation of 5-
(w-phenylalkyl) substituted 2-thiophenealde-
hydes (224) with benzyl cyanides and
hydrolysis and desulfurization of the acids
obtained (225). In this way, a,o-
diphenylcaprylic acid has been prepared.
[Pg.110]
Phenylacetic acid (phenylethanoic acid, 11),
the simplest example of this type of
compound, is prepared from benzyl chloride
by the displacement of chloride by cyanide
ion and subsequent hydrolysis to the acid
(Scheme 5.13). [Pg.65]
When only small quantities of the acid are
required, the following modi;ied procedure is
of value. One hundred grams of benzyl
cyanide are added to a mixture containing ioo
cc. of water, ioo cc. of concentrated sulfuric
acid, and ioo cc. of glacial acetic acid. After
this has been heated for forty-;ive minutes
under a re;lux condenser, the hydrolysis is
practically complete. The reaction mixture is
then poured into water, and the phenylacetic
acid isolated in the usual manner. [Pg.33]
Phenylacetonitrile (benzyl cyanide) was the
;irst compound reported to undergo phase
transfer alkylation and is probably the most
abundantly studied example of this
procedure [ 1 ]. It is a good substrate for
study because it is reasonably acidic, but not
readily alkylated by aqueous sodium
hydroxide in the absence of catalyst at any
synthetically useful rate. It has the further
advantage that it can be mono-or dialkylated
depending on conditions and it, like most
nitriles, is not prone to rapid hydrolysis. It is a
versatile synthetic intermediate, however, in
the sense that the nitrile function can be
hydrolyzed, reduced, or added to by
organometallics after an alkylation has been
carried out. [Pg.139]
Reaction of the imine 75, from 3,4-
dimethoxybenzaldehyde and amino-acetal,
with benzoyl chloride and potassium cyanide
leads to the open-chain Reissert analog 76.
This analog can be alkylated with benzyl
chloride in the presence of
dimethylformamide, but acid hydrolysis of
the alkylation product leads to 77. [Pg.206]
There are a few data in the literature to
suggest that the hydrolysis of aliphatic
nitriles occurs in mammals, but only as a
minor or even undetectable pathway in
competition with oxidative denitrilation. For
example, benzyl cyanide (11.80, Fig. 11.12)
undergoes cytochrome P450 catalyzed
hydroxy-lation to mandelonitrile (11.81),
from which cyanide and benzaldehyde are
produced, the latter being oxidized to benzoic
acid (11.83) [118]. However, a careful
metabolic study of mandelonitrile has shown
that, in the rat, this pathway accounts for ca.
90% and not 100% of the dose [122], Only ca.
10% of orally administered benzyl cyanide
was converted to mandelic acid (11.82, Fig.
11.12) by hydrolysis of the CN
group. [Pg.720]
They are both chrysanthemic acid esters of
(5-benzylfuran-3-yl)methanol (Elliott
alcohol, 1) [15]. Patented methods [16] for
the industrial preparation of Elliotf s alcohol
are demanding or such as to be hardly
exploited in industrial-scale plants. For
instance, in one of these methods [17] (5-
benzyl-3-furyl)methanol is obtained by a
sequence of Claisen condensation of benzyl
cyanide and a dialkyl succinate, hydrolysis,
esteri;ication, protection of the ketone group,
formylation, cyclization to 5-benzyl-3-
furfuryl ester and reduction to alcohol with
lithium aluminium hydride. [Pg.553]
Homogeneous, aqueous tv o-phase catalysis
is also of industrial interest for the
production of the important intermediate
phenylacetic acid (PAA), -which is used in
perfume and pesticides syntheses. The
previous process (benzyl chloride to benzyl
cyanide -with hydrolysis of the latter)
suffered from the formation of large amounts
of salt (1400 kg per kg of PAA). The new
carbonylation method reduces the amount of
salt by 60% and makes use of the great cost
difference between —CN and —CO [79-81].
Finally, the Suzuki coupling of aryl halides
and arylboronic acids, substituting
Pd/TPPMS with Pd/TPPTS catalysts, should
be also mentioned. [Pg.84]
Increasing the temperature to 350 °C results
in decarbonylation of the phenylpyruvic acid
methyl ester derivatives and the phenyl acetic
ester is formed with a ratio of 65 % a-
ketoester to 35 % acetic acid ester. Until now
the industrial process for the synthesis of
phenylacetic acid ester has started from
benzyl chloride, which is converted to benzyl
cyanide by KCN, followed by hydrolysis. Every
step of this reaction must be performed in a
separate reactor and special measures must
be taken for handling large amounts of toxic
KCN. The new route is certainly an
environmentally benign alternative
[8,27]. [Pg.222]
See other pages where Benzyl cyanide
hydrolysis to acid is mentioned: [Pg.762]
[Pg.762] [Pg.100] [Pg.205]
[Pg.292] [Pg.84] [Pg.762] [Pg.73]
[Pg.230] [Pg.57] [Pg.1079]
[Pg.762] [Pg.205] [Pg.712]
[Pg.322] [Pg.1238] [Pg.670]
See also in sourсe #XX -- [ Pg.761 ]
See also in sourсe #XX -- [ Pg.761 ]
See also in sourсe #XX -- [ Pg.761 ]
See also in sourсe #XX -- [ Pg.761 ]
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Acid cyanides
Benzyl cyanide
Benzyl cyanide hydrolysis
Benzyl hydrolysis
Hydrolysis, amide to acid of
benzyl cyanide
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