VI.

COMPUI CARBONILICI CU GRUPRI (OH)

VI.1. Aldehide i Cetone fenolice

vanilina

salicilaldehida

Preparare

Fructul de vanilie

O-Na+

1. Reactia Reimer-Tiemann

OH
+ CHCl3

OH
CHO
+

NaOH

CHO

CHCl3 + NaOH
O

..
CCl2
H

CCl2
O

O
CCl2
H

CHO

2. Sinteza Gattermann
- cu acid cianhidric
Cl
C NH HCl

H C N + 2 HCl
Acid cianhidric

H
OCH3

OCH3

OCH3
Cl
C NH HCl

H2O

HCl

- NH3

H
Anisol

CH NH HCl

CHO

- cu nitrili
Cl
OH

Cl
+

C NH HCl
R

Fenol

C NH HCl

R C N + 2 HCl
Nitril

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
H3C
O
p-Hidroxiacetofenona

4. Metoda oxidativ
OH

OH
OCH3

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

HO

25oC

CH3O

CH3O
guaiacol

aer
cat.

acid glioxilic

HO
CH3O

CH COOH
OH

C COOH
O

H
- CO2

HO
CH3O

CHO
vanilina

 0btinerea
vanilinei din
ape sulfitice
care contin
lignina
(celuloza
din lemn)
- prin
tratare cu
baze

Structura ligninei

ag. de oxidare

Vanilina