ALDEHIDE I CETONE FENOLICE

salicilaldehida

vanilina

Preparare

O-Na+

OH

1. Reactia Reimer-Tiemann
+ CHCl3

OH
CHO
+

NaOH

CHO

CHCl3 + NaOH
O

..

CCl2
H

CCl2
O

O
CCl2
H

CHO

2. Sinteza Gattermann
- cu acid cianhidric
Cl
H C N + 2 HCl
Acid cianhidric

C NH HCl

H
OCH3

OCH3

OCH3
+

Cl

C NH HCl

H2O

HCl

- NH3

H
Anisol

CH NH HCl

CHO

- cu nitrili
Cl
OH

R C N + 2 HCl
Nitril

Cl
R

Fenol

C NH HCl

C NH HCl

R
OH
HCl

OH
H2O
- NH3

R C NH HCl

R C=O

3. Transpoziia Fries
O AlCl3]- +COCH3

OCOCH3

OH
~ H+

AlCl3
H

COCH3

C
H 3C
O
p-Hidroxiacetofenona

4. Metoda oxidativ
OH
OCH3

OH

CH CH CH3
Izoeugenol

OCH3

ox.

CHO
Vanilin

O CH2
O

ox.

CH CH CH3
Izosafrol

O CH2
O

CHO
Piperonal

5. Reactia Vilsmeier

Metoda industriala de obtinere a vanilinei

HO
+

OHC COOH

CH3O
guaiacol

aer
cat.

CH3O

CH COOH

acid glioxilic

HO
CH3O

HO

25oC

OH
+

C COOH
O

H
- CO2

HO
CH3O

CHO
vanilina

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

C O
cetona

R CH

NH2
-aminoalcool

aldehida
R

OH - H2O

+ NH3

R
R

R CH=NH
aldim ina

OH - H2O

NH2

-aminoalcool

C NH

cetimina

- -Aminoalcoolii- stabili, actiune biologica

NH3
O
Etilenoxid

HO-CH2-CH2-NH2

HO-CH2-CH2

NH

HO-CH2-CH2
Monoetanolamina

Dietanolamina

Solventi, creme

HO-CH2-CH2
HO-CH2-CH2

HO-CH2-CH2
Trietanolamina

CH3-NH2 HO-CH2-CH2
O

HO-CH2-CH2

N-CH3

N-metil-dietanolamina

+SOCl2 Cl-CH2-CH2
-HCl
-SO2

Cl-CH2-CH2

N CH3

Azotiperita

Medicament anticancer
(CH3)3N] OH +

( CH3)3N CH2CH2OH] OH
Acetilcolina

HO
HO

neurohormon al sistemului nervos parasimpatic

CH CH2-NH-CH3
OH
Adrenalina

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

D(-) Efedrina

L(+) Efedrina

CH3
H3C-NH C H
H C OH

D(-) Pseudoefedrina

CH3
H C NH-CH3
HO C H

L(+) Pseudoefedrina

Aminofenoli

OH

NO2
+

HNO3

OH
red.

OH

OH

OH

red.

NO2
NH2

Paracetamol
NH2
p-Aminofenol

o-Aminofenol

Paracetamol