O

OH

Cl

O
OH

DMF (cat.)
O
O
OH

Cl

K
NH2

MeOH
pyridine
O O

SOCl2

HNO3
H2SO4
O

Cl

O
NH2

O
O 1) PhLi
2) NH4Cl
OH

1) NaNO2/HCl
H+

2) H3PO2

HO
O

4.

H2N

NH2

OH
M

When acetone is treated with diluted acid, aldol condensation produces 4-methylpent-

3-en-2-one (P).
O

H3 O +

O
P

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