ALDEHIDE I CETONE FENOLICE

Preparare
1. Reactia Reimer-Tiemann
vanilina salicilaldehida
O
-
Na
+
CHCl
3
NaOH
OH
CHO
OH
CHO
+
+
CCl
2
O O
H
O
H
CCl
2
O
CHO
CHCl
3
+ NaOH
..
CCl
2
2. Sinteza Gattermann
H C N + 2 HCl
C NH HCl
H
Cl
Acid cianhidric
- cu acid cianhidric
OCH
3
OCH
3
CH NH HCl
HCl
H
2
O
OCH
3
CHO
C NH HCl
H
Cl
+
- NH
3
Anisol
- cu nitrili
R C N + 2 HCl
C NH HCl
Cl
R
OH OH
C R NH HCl
HCl
H
2
O
OH
C=O R
+
- NH
3
C NH HCl
Cl
R
Nitril
Fenol
3. Transpoziia Fries
OCOCH
3
AlCl
3
OH
C
O H
3
C
p-Hidroxiacetofenona
O AlCl
3
]
-

+
COCH
3
H
O
H COCH
3
~ H
+
4. Metoda oxidativ

OH
OCH
3
CH CH CH
3
ox.
OH
OCH
3
CHO
Izoeugenol
Vanilin
O
O
CH
2
CH CH CH
3
O
O
CH
2
CHO
ox.
Izosafrol Piperonal
5. Reactia Vilsmeier
Metoda industriala de obtinere a vanilinei
HO
CH
3
O
+ OHC COOH
25
o
C
HO
CH
3
O
CH
OH
COOH
HO
CH
3
O
C
O
COOH
aer
cat.
H
+
- CO
2
HO
CH
3
O
CHO
guaiacol acid glioxilic
vanilina
0btinere din ape sulfitice ( celuloza din lemn) care contin lignina prin tratare
cu baze
Structura ligninei
AMINOALCOOLI I AMINOFENOLI
Aminoalcooli
- -Aminoalcooli- instabili
R CH
OH
NH
2
R CH=NH
R
C
R
OH
NH
2
- H
2
O
R
C
R
NH
- H
2
O
R
C
R
O
+ NH
3
cetona -aminoalcool cetimina
R CH=O
+ NH
3
aldehida -aminoalcool aldimina
- -Aminoalcoolii- stabili, actiune biologica
NH
3
HO-CH
2
-CH
2
-NH
2
HO-CH
2
-CH
2
NH
HO-CH
2
-CH
2
HO-CH
2
-CH
2
N HO-CH
2
-CH
2
HO-CH
2
-CH
2
O
O
O
Etilenoxid Monoetanolamina Dietanolamina Trietanolamina
Solventi, creme
HO-CH
2
-CH
2
N-CH
3
HO-CH
2
-CH
2
2
CH
3
-NH
2
+SOCl
2
Cl-CH
2
-CH
2
N
Cl-CH
2
-CH
2
CH
3
-HCl
-SO
2
O
N-metil-dietanolamina
Azotiperita
Medicament anticancer
(CH
3
)
3
N] OH +
)
3
N CH
2
CH
2
OH] OH
(
CH
3
O
Acetilcolina
neurohormon al sistemului nervos parasimpatic
HO
HO
CH
OH
CH
2
-NH-CH
3
Adrenalina
CH
3
C NH-CH
3
C OH H
H
CH
3
C H
C H HO
H
3
C-NH
CH
3
C NH-CH
3
H
C H HO
CH
3
C H
C OH H
H
3
C-NH
D(-) Efedrina L(+) Efedrina
D(-) Pseudo-
efedrina
L(+) Pseudo-
efedrina
Aminofenoli
OH
HNO
3
OH
NO
2
OH
NO
2
red.
red.
OH
NH
2
OH
NH
2
+
o-Aminofenol
p-Aminofenol
Paracetamol
Paracetamol