Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Allyl Alcohol | HCID 7858 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-Nitrobenzeneacetyl chloride | HCID 523225 | — |
| Product | Allyl 2-(3-nitrophenyl)acetate | HCID 86182979 | 81% |
Reaction Steps
To a solution of allyl alcohol (48.3 g, 56.5 ml, 831 mmol, Eq: 10) and triethylamine (12.6 g, 17.4 ml, 125 mmol, Eq: 1.5) at 0° C. was added 2-(3-nitrophenyl)acetyl chloride (intermediate B2a) (16.59 g, 83.1 mmol, Eq: 1.00) and the mixture was stirred at 0 to 23° C. for 2 h. Poured into water, extracted with ethyl acetate, washed organic layer with brine and dried over Na2SO4. Removal of the solvent in vacuum left a light brown oil, which was purified by silica gel flash chromatography with n-heptane/ethyl acetate to give the title compounds as a yellow liquid (14.89 g, 81%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08927535B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-da938b9d82184e988bda895e857c1e1c |
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| Source note | uspto-grants-2015_01 |
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