Ethylene Glycol → HCID 59318308, compound

HRID 561085Notes

Reaction equation

HRID 561085 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-3f9858e85f9644b58bfdc36e5acef136
Source dataset
uspto-grants-2011_11
Patent number
US08063223B2

Reaction notes

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