Ethylene Glycol → HCID 59318308, compound

HRID 1518101Notes

Reaction equation

HRID 1518101 reaction equation
[CH2:1]([OH:4])[CH2:2][OH:3].[CH:5]([O-:9])([O-])[O:6][CH3:7].[OH2:10].[C:11]1([CH3:21])[CH:16]=[CH:15][C:14](S(O)(=O)=O)=[CH:13][CH:12]=1.[C:22]1([CH3:28])C=CC=C[CH:23]=1>>[O:3]1[CH2:2][CH2:1][O:4][C:28]21[C:15]1[C:14](=[CH:13][CH:12]=[C:11]([CH2:21][C:5]([O:6][CH3:7])=[O:9])[CH:16]=1)[O:10][CH2:23][CH2:22]2

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 1140Toluene2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 53629101Methylorthoformate

Product 1

HCID 59318308HCID 59318308, compound

Procedure

A solution of the compound (7-1-4) (419 mg, 1.9 mmol), ethylene glycol (0.21 mL, 3.8 mmol), Methyl orthoformate (0.42 mL, 3.8 mmol), and p-Toluenesulfonic acid monohydrate (72 mg, 0.38 mmol) in toluene (8 mL) was heated under reflux for 3 hours. After cooling to room temperature, toluene (10 mL) was added thereto, and the mixed solution was washed with an aqueous saturated sodium bicarbonate solution (10 mL), water, and brine in this order. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure to obtain a crude product of the title compound (502 mg).

Workup

  1. temperatureunder reflux for 3 hours
  2. washthe mixed solution was washed with an aqueous saturated sodium bicarbonate solution (10 mL), water, and brine in this order
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-16315b83092f48ea8b3cb91f43be3317
Source dataset
uspto-grants-2012_07
Patent number
US08232405B2

Reaction notes

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