Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 1-Naphthol | HCID 7005 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | Tert-Butyl hypochlorite | HCID 521297 | — |
| Reactant | HCID 22144312 | HCID 22144312 | — |
| Solvent | Carbon Tetrachloride | HCID 5943 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 66632715 | HCID 66632715 | 43% |
Reaction Steps
A solution of 4-pentyloxy-naphthalene-1-carbaldehyde (121 mg,.0.5 mmol) in CCl4 (2 mL) is treated with t-BuOCl (8.82 M, 170 μL, 1.5 mmol) and stirred at 50° C. for 1 h. After addition of DIEA (0.3 mL, 1.7 mmol) and 1-naphthol (216 mg, 1.5 mmol) the mixture is refluxed for 2 h and distributed between 1M KHCO3 (5 mL) and DCM (2×5 mL). The combined organic phases are dried over Na2SO4 and concentrated. Flash chromatography (cyclohexane/acetone) yields 82 mg (43%) of colourless crystals.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07045533B2 |
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| Source dataset | uspto-grants-2006_05 |
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| ORD ID | ord-01ce5b6503204aaabadcedfd2f632bb7 |
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| Source note | uspto-grants-2006_05 |
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