Synthesis and characterization of (E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol from 2-hydroxy-4,5-dimethylacetophenone

Article abstract of DOI:10.1007/s12039-020-01802-4

This study reports the development of a novel substituted hydrazone prepared from 2-hydroxy-4,5-dimethylacetophenone and hydrazine in alkaline medium at controlled conditions which yields as corresponding hydrazone [(E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol]. The structure of synthesized (E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol was elucidated by elemental analysis and spectroscopic techniques like infrared spectroscopy, ultraviolet–visible spectroscopy, high-performance liquid chromatography, proton nuclear magnetic resonance and mass spectrum.

Full text of DOI:10.1007/s12039-020-01802-4

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3 . 3 Infrared analysis: (E)-2-(1-hydrazonoethyl)-
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H3C
H3C
H3C
H3C
O
160-180°C
Ethanol
Cl
CH3
+
O
CH3
O
OH
3,4-dimethylphenol
Chemical Formula: C8H10
Molecular Weight: 122.16
acetyl chloride
Chemical Formula: C2H3ClO
Molecular Weight: 78.50
3,4-dimethylphenyl acetate
Chemical Formula: C10H12O2
Molecular Weight: 164.20
O
Scheme 1.
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J. Chem. Sci.
(
2
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2
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1
3
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:
8
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P
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O
H3C
H3C
H3C
H3C
HCl
O
CH3
OH
+ AlCl3
Ethanol
O
CH3
3,4-dimethylphenyl acetate
Aluminium Chloride
Chemical Formula: C10H12O2 Chemical Formula: AlCl3
1-(2-hydroxy-4,5-dimethylphenyl)ethanone
Chemical Formula: C10H12O2
Molecular Weight: 164.20
Molecular Weight: 164.20
Molecular Weight:133.34
Scheme 2.
e t h an o n e .
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H3C
H3C
Methanol
Acetic Acid
H3C
H3C
CH3
NH2
NH2
CH3
Reflux
Heat
OH
1-(2-hydroxy-4,5-
dimethylphenyl)ethanone
Chemical Formula: C10H12O2
Molecular Weight: 164.20
OH
hydrazine
(E)-2-(1-hydrazonoethyl)-4,5-dimethylphenol
Chemical Formula: C10H14N2O
Molecular Weight: 178.23
Chemical Formula: H4N2
Molecular Weight: 32.05
Scheme 3.
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Table 1.
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l
l
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p
o
w
d
e
r
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l
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r
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a
f
o
n
r
o
m
6
3
°
C
–
6
8
°
C
7
6
%
1
,
5
i
m
t
h
e
n
l
u
i
n
h
a
l
,
t
h
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,
D
M
S
O
,
e
t
h
y
l
a
n s o l u b l e i n w a t e r
c
e
t
a
t
e
I
Table 2.
M
a
s
s
a
n
a
l
y
s
i
s
.
H
y
d
r
a
z
o
n
e
M
o
l
e
c
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l
a
r
f
o
r
m
u
l
a
M
o
l
e
c
u
l
a
r
w
3
e
i
g
h
t
M
o
l
e
c
u
l
a
r
i
o
n
p
e
a
k
(
/
e
)
(
E
)
-
2
-
(
1
-
h
y
d
r
a
z
o
n
o
e
t
h
y
l
)
-
4
,
5
-
d
i
m
e
t
h
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l
p
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n
o
l
C
H
N
O
1
7
8
.
2
1
7
9
.
2
1
0
1
4
2
T
h
n
h
d
e
m
I
e
R
s
p
o
m
e
f
c
t
r
a
(
u
t
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l
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n
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t
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r
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a
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y
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h
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b
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b
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m
m
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e
T
o
2 5 .
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P
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a
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5
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P
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2 3 3 H 1 4 0 9 C S p e ct ro p h o t o -
f
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)
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4
.
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h
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a
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s
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t
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r
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c
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s
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V
(
b
a
n
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s
m
x
i
m
m
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m
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i
n
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t
h
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l
:
2
5
4
,
t
r
u
m
r
e
s
h
o
w
n
g
u
r
3
.
3
3
.
dimethylphenol
4
U
V
a
n
a
l
y
s
i
s
:
(
E
)
-
2
-
(
1
-
h
y
d
r
a
z
o
n
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e
t
h
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l
)
-
4
,
5
-
3 . 5 Elemental analysis (CHNS): (E)-2-(1-
hydrazonoethyl)-4,5-dimethylphenol
T
h
m
e
U
V
s
p
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e
n
c
o
t
r
l
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f
m
t
p
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u
(
n
E
d
)
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2
n
-
(
m
1
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r
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t
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d
-
F
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r
m
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t
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n
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fi
y
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d
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r
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t
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i

8
8
P
a
g
e
4
o
f
8
J. Chem. Sci.
(
2
0
2
0
)
1
3
2
:
8
8
Figure 1.
M
a
s
s
s
p
e
c
t
r
u
m
o
f
(
E
)
-
2
-
(
1
-
h
y
d
r
a
z
o
n
o
e
t
h
y
l
)
-
4
,
5
-
d
i
m
e
t
h
y
l
p
h
e
n
o
l
.
1
Figure 2.
H
N
M
R
s
p
e
c
t
r
u
m
o
f
(
E
)
-
2
-
(
1
-
h
y
d
r
a
z
o
n
o
e
t
h
y
l
)
-
4
,
5
-
d
i
m
e
t
h
y
l
p
h
e
n
o
l
.

J. Chem. Sci.
(
2
0
2
0
)
1
3
2
:
8
8
P
a
g
e
5
o
f
8
8
8
1
Table 3.
H
N
M
R
a n a l y s i s .
A
s
s
i
g
n
m
e
n
t
s
C
h
e
m
i
c
a
l
s
h
i
f
t
(
p
p
m
)
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u
n
c
t
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n
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r
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p
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o
.
o
f
p
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t
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n
M
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l
t
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p
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c
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t
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a
b
e
1
2
7
6
1
.
.
.
.
–
1
4
1
7
2
8
6
0
3
.
4
7
9
6
–
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–
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H
1
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r
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t
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2
.
1
9
2
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1
M u l t i p l e t
i
3
g
5
N
H
B
r
o
a
d
,
s
n
g
l
e
2
Table 4.
I
R
a
n
a
l
y
s
i
s
.
–
1
B
o
n
d
/
f
u
n
c
t
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o
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a
l
g
r
o
u
p
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r
e
q
u
e
n
c
y
,
c
m
C
C
C
N
C
C
–
=
–
–
–
–
–H
O
C
C
H
H
H
1 2 3
1 4 4
1 5 0
1 5 9
2 9 2
3 0 5
3 6 3
0
(
a
r
o
m
a
t
i
c
r
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n
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)
7
6
4
2
0
0
s
s
t
t
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r
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e
t
t
c
c
h
h
a
a
l
k
e
m
n
e
a
s
r
o
t
i
c
s
Figure 4.
d i m e t h y l p h e n o l .
U
V
s
p
e
c
t
r
u
m
f
o
r
(
E
)
-
2
-
(
1
-
h
y
d
r
a
z
o
n
o
e
t
h
y
l
)
-
4
,
5
-
O
3
dimethylphenol
.
6 Water content: (E)-2-(1-hydrazonoethyl)-4,5-
w
h
i
ch
w
a
s
r
e
c
o
r
d
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d
b
y
V
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r
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l
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r
.
T
h
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t
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l
l
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5
n
-
t
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l
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p
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d
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)
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-
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m
-
(
a
1
r
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h
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d
d
r
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o
-
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h
)
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4
,
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t
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l
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e
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n
T
h
5
e
-
w
a
e
t
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r
c
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n
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t
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c
f
t
o m p o u n d i n m et h a n o l w as
h
e
(
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)
-
2
-
(
1
-
h
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d
r
a
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n
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t
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y
l
)
-
T
a
b
l
e
5
.
4
,
d
i
m
t
h
y
l
p
Figure 3.
I
R
s
p
e
c
t
r
u
m
o
f
(
E
)
-
2
-
(
1
-
h
y
d
r
a
z
o
n
o
e
t
h
y
l
)
-
4
,
5
-
d
i
m
e
t
h
y
l
p
h
e
n
o
l
.

8
8
P
a
g
e
6
o
f
8
J. Chem. Sci.
(
2
0
2
0
)
1
3
2
:
8
8
Table 5.
C
a
r
b
o
n
,
h
y
d
r
o
g
e
n
,
n
i
t
r
o
g
e
n
,
s
u
l
p
h
u
r
e
l
e
m
e
n
t
a
l
a
n
a
ly
z
e
r
.
E
l
e
m
e
n
t
a
l
d
a
t
a
(
r
e
q
u
i
r
e
d
/
f
ou
n
d
)
H
y
d
r
a
z
o
n
e
M
o
l
e
c
u
l
a
r
f
o
r
m
u
l
a
M
o
l
e
c
u
l
a
r
w
3
e
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g
h
t
C
a
r
b
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n
H
y
d
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g
e
n
N i t ro g en
(
E
)
-
2
-
(
1
-
h
y
d
r
a
z
o
n
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e
t
h
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l
)
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4
,
5
-
d
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m
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t
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l
p
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l
C
H N O
0 1 4 2
1
7
8
.
2
6
(
7
6
.
7
1
.
6
3
7
(
.
7
8
.
5
9
1
5
5
.
6 8
.
1
9
)
2
)
(
1
7
2
)
Table 6.
P
u
r
i
t
y
,
H
P
L
C
a
n
a
l
y
s
i
s
d
e
t
a
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l
s
.
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P
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C
s
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m
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m
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P
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C
F l
W
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l
l
w
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m
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h
0
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n
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n
C
1
8
,
1
0
0
A
,
4
.
6
m
m
9
2
5
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m
m
,
5
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r
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g
1
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4
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1
3
.
5
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m
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t
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p
p
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m
r
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t
t
u
u
r
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e
0
°
C
C
S
a
m
l
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m
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5
°
I
n
j
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t
t
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0 l
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m
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n
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r
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0
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t
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s
M
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b
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p
h
a
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A
(
%
)
M
o
b
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(
%
)
9
2
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1
0
1
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1
2
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1
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%
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g
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0
.
3
%
w
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t
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r
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.
H
u
m
a
n
U
s
e
(
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CH
)
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t
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p
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t
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f
w
a
3
.
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Acknowledgements
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h
e
a
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t
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