Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1,3-Propanediol | HCID 10442 | — |
| Reactant | alpha-Bromo-o-chlorotoluene | HCID 11905 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | Ethyl acetate hexane | HCID 21226206 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18673603 | HCID 18673603 | 35.8% |
Reaction Steps
3.7 g(49 mmol) of 1,3-propandiol was dissolved in 50 ml of dimethylformamide and cooled to 0° C. 2 g(50 mmol) of 60% sodium hydride dispersed in mineral oil was added slowly. After the mixture was stirred for 10 minutes, 10 g(49 mmol) of 2-chlorobenzyl-bromide dissolved in 10 ml of dimethyformamide was added slowly. After stirring for one hour at room temperature, dimethylformamide was removed under reduced pressure, 100 ml of ethylacetate was added to the residue and the organic layer was washed with saturated sodium chloride solution (100 ml×3). The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to column chromatography(eluent: n-hexane/ethylacetate=4/1, v/v) to give 3.52 g(Yield 35.8%) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06511978B1 |
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| Source dataset | uspto-grants-2003_01 |
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| ORD ID | ord-5adbafcb454c4138b734bc549fd018ff |
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| Source note | uspto-grants-2003_01 |
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