Hydrochloric Acid → (2-(2-Methoxyethoxy)ethoxy)acetic acid

A 0.5 g quantity of platinum oxide is hydrogenated in 60 ml of water at 25° C. and atmospheric pressure until the uptake of hydrogen ceases. To the resultant mixture is added a mixture of 0.6 g (7.14 mmoles) of sodium bicarbonate and 1.0 g (6.1 mmoles) of triethylene glycol monomethyl ether dissolved in 20 mL of water. Air is bubbled through the above mixture for 4 hr following the consumption of staging material by TLC. The reaction is then filtered though Celite and the Celite washed with water. The combined washes are treated with 7.2 mL (7.2 mmoles) of 1N hydrochloric acid and the resultant solution freeze-dried. The residue is washed with acetone and filtered. The filtrate is evaporated to dryness under vacuum. The residual oil is chromatographed over 100 g of CC-4 silica gel eluted with (50-50)acetone-methylene chloride, collecting 20 mL fractions. Concentration of fractions 11-16 gives 0.92 g of the desired 3,6,9-trioxadecanoic acid.

1. customAir is bubbled through the above mixture for 4 hr
2. customthe consumption of staging material by TLC
3. filtrationThe reaction is then filtered though Celite
4. washthe Celite washed with water
5. dry with materialthe resultant solution freeze-dried
6. washThe residue is washed with acetone
7. filtrationfiltered
8. customThe filtrate is evaporated to dryness under vacuum
9. customThe residual oil is chromatographed over 100 g of CC-4 silica gel
10. washeluted with (50-50)acetone-methylene chloride
11. customcollecting 20 mL fractions

ORD record

ord-14f7b9a478c54cdda34d28627377fd52

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05739350