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A solution of 5.46 g (0.048 mole) of squaric acid in 250 ml of
water was neutralized with 1 N sodium hydroxide and treated with a
solution of 16.3 g (0.096 mole) of silver nitrate in 100 ml of water.
The light yellow precipitate of disilver squarate was filtered and
washed with water, acetone, and ether. Concentration of the filtrate led to additional silver squarate,
which was soluble to the extent of about 0.4%.
The dried silver salt was boiled for 2 hr in
25 ml of methyl iodide and 50 ml of ether and shaken for 2 days.
The mixture was filtered. the residue was washed with ether, and the
ether was concentrated, leading to Ib, 5.45 g (0.038 mole, 79%
yield), mp 56.7-58.0", fluffy white crystals, soluble in methanol and
benzene. Infrared absorption bands (potassium bromide pellet)
were at 3.5. 5.55, 5.8, 6.3. 6.75, 7.1, 7.35, 8.2. 8.75, 9.2, 9.65. 10.65, I . , I . . . , , ,
10.75, and 12 p.

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