Diethylene Glycol Monomethyl Ether → Carbonic acid, 2-(2-methoxyethoxy)ethyl methyl ester

HRID 248663Notes

Reaction equation

HRID 248663 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6]CO.[C:9](=[O:14])([O:12][CH3:13])[O:10][CH3:11].C[O-].[Na+]>>[C:9](=[O:14])([O:12][CH2:13][CH2:1][O:2][CH2:3][CH2:4][O:5][CH3:6])[O:10][CH3:11]

Participants

4

Reactant 3

HCID 8134Diethylene Glycol Monomethyl Ether2×HCID 12021Dimethyl CarbonateHCID 10942334Sodium Methoxide

Product 1

HCID 10888474Carbonic acid, 2-(2-methoxyethoxy)ethyl methyl esterYield 90%

Conditions

Temperature
84 °C

Procedure

A total of 144.2 grams (1.2 mol) of 2-(2-methoxyethoxy)ethanol, 400 grams (4.4 mol) of dimethyl carbonate and 3 grams (0.05 mol) of sodium methoxide were combined in a 1-liter 3-neck round bottom flask equipped with a 14 inch distillation column, distillation head, and magnetic stirbar. The system was evacuated and purged three times with nitrogen using a Firestone valve, and left under a constant nitrogen atmosphere. After a period of 1.5 hours at reflux (kettle temperature 84° C.), methanol (boiling point 64° C.) was slowly removed overhead to drive the equilbrium. A total of 49.8 grams of methanol was removed over a period of 3 hours, after which time the stopcock was closed and the reaction mixture was allowed to reflux overnight. The mixture was then cooled to room temperature, filtered and charged (429 grams) to a 500 milliliter round bottom flask equipped with a distillation head and magnetic stirbar. Excess dimethyl carbonate (boiling point 90° C.) was removed overhead. The flask was then cooled, put under vacuum (10-11 mm Hg , and methyl 2-(2-methoxyethoxy)ethyl carbonate removed overhead (boiling point 115°-125° C.). A total of 193 grams (ca. 90% yield) was obtained. Gas chromatography analysis of this material showed 97.74% purity (remainder was 2-(2-methoxyethoxy)ethanol).

Workup

  1. customequipped with a 14 inch distillation column, distillation head, and magnetic stirbar
  2. customThe system was evacuated
  3. custompurged three times with nitrogen using a Firestone valve
  4. waitleft under a constant nitrogen atmosphere
  5. customA total of 49.8 grams of methanol was removed over a period of 3 hours
  6. customafter which time the stopcock was closed
  7. temperatureto reflux overnight
  8. temperatureThe mixture was then cooled to room temperature
  9. filtrationfiltered
  10. additioncharged (429 grams) to a 500 milliliter round bottom flask
  11. customequipped with a distillation head and magnetic stirbar
  12. customExcess dimethyl carbonate (boiling point 90° C.) was removed overhead
  13. temperatureThe flask was then cooled
  14. customremoved overhead (boiling point 115°-125° C.)
  15. customA total of 193 grams (ca. 90% yield) was obtained

Sources & evidence

ORD record
ord-098f750de5a84d9591328f9f07e7e284
Source dataset
uspto-grants-1993_05
Patent number
US05210322

Reaction notes

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