Page 1090 - Advanced Organic Chemistry Part B - Reactions & Synthesis

1066 Scheme 12.1. Oxidation with Chromium(VI) Reagents

CHAPTER 12 A. Chromic acid solutions
Oxidations
H CrO 4
2
1 a CH CH CH OH CH 3 CH 2 CH O
3
2
2
H O 45–49%
2
2 b OH H CrO 4 O
2
acetone
92–96%
3 c CH(CH ) CH(CH 3 ) 2
3 2
OH H CrO 4 O
2
acetone
84%
CH
CH 3 3
4 d OH H CrO 4
2
O
acetone
79–88%
B. Chromium trioxide–pyridine
3
5 e CrO –pyridine
(CH ) CH OH CH (CH ) CH
CH 3 2 5 2 3 2 5 O
CH Cl 2 70–84%
2
6 f
CH 3 CH 3
CrO –pyridine
3
CH CH CH(CH ) CH OH CH CH CH(CH ) CH O
2
3
2 4
2 4
2
2
3
CH Cl 2 69%
2
7 g OH O
H C H C
3
CrO –pyridine 3
3
H C CH Cl 2 H C
2
2
2
CH 3 CH 3 CH 3 CH 3 95%
8 h CH 3 CH 3
CrO –pyridine
3
Cl CH
CH 3 CH 2 2 3
CH 2 CH
CH 3 OH CH 3 CH 3 O CH 3
9 i CH O
O 3
CH 3
CH 3 O O CrO –pyridine CH 3 O O
3
O O
HO CH 3 CH CO H CH 3
3
2
O MS 4A O O CH
CH 3 3
96%
(Continued)