Table 2.

Synthesis of chlorinated derivatives of 3,4,6-trimethoxy-1-methyl-9H-xanthen-9-one (7).

Comp.	R1	R2	R3	R4	R5	R6	Method	Yield (%)
12	CH3	Cl	OCH3	H	OCH3	H	A D E	7 12 14
13	CH3	Cl	Cl	H	OCH3	H	A B C	Traces 12 8
14	CH2Cl	H	OCH3	H	OCH3	H	A B D	Traces 8 13
15	CH3	H	Cl	H	OCH3	H	B C	5 10
16	CH3	H	Cl	H	Cl	H	C	6
17	CH3	Cl	OCH3	Cl	OCH3	H	E	traces
18	CH3	Cl	OCH3	H	OCH3	Cl	E	traces
19	CH3	H	OCH3	Cl	OCH3	H	E	5
20	CH3	H	OCH3	H	OCH3	Cl	E	1

Method A: SOCl₂, r.t, seven days; Method B: SOCl₂, 40 °C, seven days; Method C: SOCl₂, ∆, seven days; Method D: NaCl, p-TsOH, NCS, H₂O, r.t., seven days; Method E: H₂O₂, AcOH, NaCl, 40 °C, seven days.