Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | N-Hydroxyphthalimide | HCID 10665 | — |
| Reactant | 2-Bromoethanol | HCID 10898 | — |
| Reactant | Sodium Acetate | HCID 517045 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 10679822 | HCID 10679822 | 66.5% |
Reaction Steps
To a solution of N-hydroxyphthalimide (2.20 g, 13.5 mmol) and sodium acetate (3.30 g) in dimethylsulfoxide (40 mL) was added 2-bromoethanol (2.88 mL) under an argon atmosphere at room temperature. The reaction mixture was stirred at 70° C. for 5 hours, followed by cooling to room temperature, adding water (40 mL), and extracting with methylene chloride. The resulting organic layer was washed with water, 2.5M hydrochloric acid, and saturated brine. The washed organic layer was dried over magnesium sulfate, the residue resulting from distilling off the solvent under reduced pressure was recrystallized with ethanol and water to afford 1.86 g of the title compound (yield 66%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09181250B2 |
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| Source dataset | uspto-grants-2015_11 |
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| ORD ID | ord-559c5cc84daa4e088a8d6db5a77b2168 |
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| Source note | uspto-grants-2015_11 |
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