ALDEHIDE ŞI CETONE FENOLICE

salicilaldehida vanilina

Preparare
O-Na+ OH OH
1. Reactia Reimer-Tiemann CHO
NaOH
+ CHCl3 +

CHO

CHCl3 + NaOH CCl2

O O O O
.. CCl2 CHO
CCl2
H H
2. Sinteza Gattermann
- cu acid cianhidric
Cl
H C N + 2 HCl C NH HCl
Acid cianhidric H

OCH3 OCH3 OCH3

Cl HCl H2O
+ C NH HCl
H - NH3
Anisol CH NH HCl CHO

- cu nitrili
Cl
R C N + 2 HCl C NH HCl
Nitril R
OH OH OH

Cl HCl H2O
+ C NH HCl
R - NH3

Fenol R C NH HCl R C=O

3. Transpoziţia Fries
OCOCH3 O AlCl3]- +COCH3 O OH

AlCl3 ~ H+

H H COCH3 C
H3C O
p-Hidroxiacetofenona

4. Metoda oxidativă

OH OH O CH2 O CH2
OCH3 OCH3
ox. O O
ox.

CH CH CH3 CHO CH CH CH3 CHO

Izoeugenol Vanilinã Izosafrol Piperonal
5. Reactia Vilsmeier
 Metoda industriala de obtinere a vanilinei

HO HO
25oC
+ OHC COOH
CH3O CH3O CH COOH
guaiacol acid glioxilic OH

HO + HO
aer H
cat. - CO2
CH3O C COOH CH3O CHO
O vanilina
 0btinere din ape sulfitice ( celuloza din lemn) care contin lignina prin tratare
cu baze

Structura ligninei
 AMINOALCOOLI ŞI AMINOFENOLI
Aminoalcooli
- α-Aminoalcooli- instabili

+ NH3 OH - H2O
R CH=O R CH R CH=NH
NH2
aldehida α-aminoalcool aldim ina

R + NH3 R OH - H2O R
C O C C NH
R R NH2 R
cetona α-aminoalcool cetimina

- β-Aminoalcoolii- stabili, actiune biologica

HO-CH2-CH2
NH3 O HO-CH2-CH2 O
HO-CH2-CH2-NH2 NH HO-CH2-CH2 N
O HO-CH2-CH2
HO-CH2-CH2
Etilenoxid Monoetanolamina Dietanolamina Trietanolamina
Solventi, creme
 CH3-NH2 HO-CH2-CH2 +SOCl2 Cl-CH2-CH2
2 N-CH3 N CH3
O HO-CH2-CH2 -HCl Cl-CH2-CH2
-SO2
N-metil-dietanolamina Azotiperita
Medicament anticancer
(CH3)3N] OH + ( CH3)3N CH2CH2OH] OH
O
Acetilcolina
HO
neurohormon al sistemului nervos parasimpatic
HO CH CH2-NH-CH3
OH
Adrenalina

CH3 CH3 CH3 CH3

H C NH-CH3 H3C-NH C H H3C-NH C H H C NH-CH3
H C OH HO C H H C OH HO C H

D(-) Efedrina L(+) Efedrina D(-) Pseudo- L(+) Pseudo-

efedrina efedrina
Aminofenoli

OH OH OH OH
HNO3 NO2 red.
+ Paracetamol

OH NO2 NH2
p-Aminofenol
NH2
red.

o-Aminofenol

Paracetamol