A Practical Large-Scale Synthesis of (1-Naphthyl)acetylene

References

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• The last traces of the solvent are removed at a pressure of 0.1 mmHg
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• Above 60 °C it was a light yellow oil. 2-(1-Naphthyl)ethanol is also commercially available; however, it is rather expensive (Aldrich: 50 g costs Hfl 152.70)
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• The 60 MHz 1H NMR spectra were recorded on a Varian EM360 apparatus using 20% solutions in carbon tetrachloride and tetramethylsilane as internal standard
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• If it fells so out, stirring at room temperature can be performed during the night
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• Omitting of the distillation of 4 results in the formation of impurities in 5, and subsequently much lower yields of 7, as in that case 5 has to be distilled, which easily polimerizes during the distillation. See also note 18
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• Olah , G. A. and Singh , B. P. 1982 . J. Am. Chem. Soc. , 104 : 5168 Bp 90 °C (0.25 mmHg) and 1H NMR (60 MHz, CDCl3) δ 7.6–8.4 (7H), 3.6–4.2 (4H) are the data of 4 reported by:
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• This heating under reflux is necessary to complete the reaction, which proceeds much slower in the end. This is due to the formation of tert-butylalcohol during the reaction, which deactivates potassium tert-butoxide by forming a 1:1 complex with it
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• The preparation of sodamide is well described in ref. 9, p21
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• The temperature of the sodamide suspension has to be established at exactly-37 °C by cooling in a bath with acetone/dry-ice. Addition at higher temperature (-33 °C) results is losses due to polymerisation, whereas lower temperatures gives rise to the formation of 1-vinylnaphthalene (5)
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• Ref. 8: 135 °C (20 mmHg); ref. 7: 45 °C (0.25 mm Hg), (the latter value was measured by distillation of an amount of 130 mg of 7)
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• Ref. 7: n 20 D 1.6360
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• Mass spectroscopy was performed on a Kratos MS80 GC-MS combination apparatus
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