Chemistry Reference
In-Depth Information
O
OEt
CH
2
CH
2
OH
1.
(COCl)
2
O
LiAlH
4
2. EtOH
H
H
H
1271
1272
1273
H
N h
CH
2
CH
2
N
O
H
Indoramin
Wyeth Ayerst
1274
The Friedel-Crafts reaction of oxalyl chloride with aromatic compounds offers a
useful means of generating aromatic carboxylic acids. The reaction essentially pro-
ceeds via a chloroglyoxylate intermediate 1278, which decomposes on heating to give
the corresponding acid chloride 1279. The similar preparation of heteroaryl carbox-
ylic acids 1282 from substrates 1281 is also reported. Yields are generally high [958].
(COCl)
2
1. CHCl
3
,
reflux
O
OH
S
S
2. H
2
O
O
1275
1276
COCO
Cl
CO
Cl
CO
OH
Me
Me
Me
Me
Me
Me
Me
Me
(COCl)
2
Reflux
H
2
O/HCl
1.
(COCl)
2
1 hr
Me
Me
Me
Me
80 %
1277
1278
1279
1280
R
R
NN
NN
AlCl
3
, CS
2
Me
Me
Me
Me
2. H
2
O
CO
OH
70-90 %
1281
1282
