Organic Reactions Volume 4 - Sciencemadness Dot Org

Acid Chloride
l-Acetoxy-3-naphthoyl chloride
4-Chloro-l-naphthoyl chloride
6-Chloro-l-naphthoyl chloride
5-Bromo-l-naphthoyl chloride
1,2,3,4-Tetrahydro-6-naphthoyl
chloride
l,2,3,4-Tetrahydro-6-acetoxy-7naphthoyl
chloride
1-Acenaphthoyl chloride
2-Phenanthroyl chloride
3-Phenanlhroyl chloride
9-Phenanthroyl chloride
9,10-Dihydro-2-phenanthroyl
chloride
2-Methoxy-9, 10-dihydro-7phenanthroyl
chloride
2-Anthraquinonecarbonyl
chloride
1,8-Diacetoxy~3-anthraquinonecarbonyl
chloride
l-Acetoxy-6-anthraquinonecarbonyl
chloride
l-Acetoxy-3-anthraquinonecarbonyl
chloride
p-Phthalyl chloride
m-Phthalyl chloride
o-Phthaiyl chloride l
1,8-Naphthalyl ohlorido
Solvent
Xylene
Xylene
Xylene
Xylene
Cymene
Xylene
Xylene
Dccalin
Decalin
Dccalin
Decalin
Decalin
Xylene
Xylene
Xylene
Xylene
Xylene
Xylene
Totralin
~
ORGANIC REACTIONS
TABLE II—Continued
AROMATIC ALDEHYDES
Temperature,
0 C
150
160
150
_
•—
150-160
180-185
180-185
180-185
180-185
180-185
150-160
150-160
130-140
140-150
150
150
150
~
Catalyst
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-BaSO4
Pd-BaSO4 *
Pd-BaSO4
Pd-BaSO4 (2%)
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-BaSO4 (5%)
Pd-kieselguhr (2.5%)
Pd-kieselguhr (2.5%)
Pd-kieselguhr (2.5%)
~
Regulator
Quinoline-S
Quinoline-S
Quinoline-S
None
—
None
Quinolino-S
None
None
None
None
None
None *
None
None
None
Quinolino-S
Quinoline-S
Quinoline-S
^
Yield of
Aldehyde,
%
70
73
63 a
—
65-70
_Ji
72
70
90
90
70
67°
57
-J
_&
—
81
83
5-6 m
0n
Reference*
14, 107
107a
107a
105
108
110
76
62
62
62
111
111
112
112
113
113
26, 25, 58
26
27,26
30
* References 85-118 are listed on pp. 376-377.
a Yield calculated on the acid employed.
b The corresponding dihydroxyaldehyde was isolated in a yield of 81%,
c Yield of vanillin 82%.
A Isolated as the dihydroxy compound.
e Reduotion was carried out with 100 g. of acid chloride.
/ Commercial xylene.
8 The same batch of catalyst was used five times. It was then reactivated by heating in a casserole
for one hour over a strong flame. On the other hand, Pd-BaSO4 has been heated to 600° for twenty
minutes in order to deactivate it partially (hydrogenation of acetylenic to olefinic bond). 109
' l The corresponding hydroxyaldehyde was isolated in a yield of about 40%.
* When ''quinoline-S'' was employed, the yield was poor.
? The corresponding dihydroxyaldehyde was isolated in a yield of 50%.
k The corresponding hydroxyaldehyde was isolated in a yield of 50%.
1 For the preparation and structure of phthalyl chloride, succinyl chloride, and related compounds,
see the papers of Ott, 114 Kirpal, Galuschka, and Lassak, 116 Martin and Partington, 116 Ott, Langenohl,
and Zerweck, 117 Kyrides, 50 and French and Kircher. 118
m The aldehyde was isolated as phthalazine derivative; by-products, phthalide and biphthalyl; main
product, resinous mass.
n The reaction product consisted of a complex mixture from which only naphthalic acid anhydride
could be isolated. The reaction was carried out under the conditions given by Rosenmund and
Zetzsche. 2