ALDEHIDE I CETONE FENOLICE

salicilaldehida

vanilina
O-Na+ OH + CHCl3 NaOH CHO + CHO

Preparare
1. Reactia Reimer-Tiemann
OH

CHCl3 + NaOH O O H

CCl2 O CCl2 H O CHO

..
CCl2

2. Sinteza Gattermann - cu acid cianhidric

Cl H C N + 2 HCl Acid cianhidric
OCH3 Cl + H Anisol C NH HCl HCl

C NH HCl H
OCH3 H2O - NH3 CH NH HCl CHO OCH3

- cu nitrili
Cl OH R C N + 2 HCl Nitril Cl + R Fenol C NH HCl HCl C NH HCl R OH H2O - NH3 R C NH HCl R C=O OH

3. Transpoziia Fries
OCOCH3 AlCl3 H O AlCl3]- +COCH3 O ~ H+ OH

C H3C O p-Hidroxiacetofenona

COCH3

4. Metoda oxidativ
OH OCH3 ox. OH OCH3 O CH2 O O CH2 O

ox.

CH CH CH3 Izoeugenol

CHO Vanilin

CH CH CH3 Izosafrol

CHO Piperonal

5. Reactia Vilsmeier

Metoda industriala de obtinere a vanilinei

HO + CH3O guaiacol HO CH3O C COOH O acid glioxilic OHC COOH

25oC

HO CH3O CH COOH OH
+

aer cat.

H - CO2

HO CH3O vanilina CHO

0btinere din ape sulfitice ( celuloza din lemn) care contin lignina prin tratare cu baze

Structura ligninei

AMINOALCOOLI I AMINOFENOLI
Aminoalcooli
- -Aminoalcooli- instabili
+ NH3

R CH=O aldehida R R C O cetona

+ NH3

R CH

OH - H2O

NH2 -aminoalcool C OH - H2O NH2

R CH=NH aldim ina R C NH R cetimina

R R

-aminoalcool

- -Aminoalcoolii- stabili, actiune biologica

HO-CH2-CH2 HO-CH2-CH2 Trietanolamina N HO-CH2-CH2

NH3 O Etilenoxid

HO-CH2-CH2-NH2 Monoetanolamina

HO-CH2-CH2 HO-CH2-CH2 Dietanolamina

NH

Solventi, creme

CH3-NH2 HO-CH2-CH2 O HO-CH2-CH2

N-CH3

+SOCl2 Cl-CH2-CH2 -HCl -SO2 Cl-CH2-CH2 Azotiperita

N CH3

N-metil-dietanolamina

Medicament anticancer
(CH3)3N] OH + O ( CH3)3N CH2CH2OH] OH Acetilcolina
HO HO CH CH2-NH-CH3 OH Adrenalina

neurohormon al sistemului nervos parasimpatic

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

CH3 H3C-NH C H H C OH

CH3 H C NH-CH3 HO C H

D(-) Efedrina

L(+) Efedrina

D(-) Pseudoefedrina

L(+) Pseudoefedrina

Aminofenoli

OH
HNO3

OH NO2 + OH
red.

OH
red.

OH

Paracetamol
NH2 p-Aminofenol

NO2 NH2

o-Aminofenol

Paracetamol