2-naphthalen-1-ylpropan-2-ol Chemical Properties

Melting point:

80 °C(Solv: ligroine (8032-32-4))

Boiling point:

130-140 °C(Press: 0.1 Torr)

Density 

1.087±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

14.36±0.29(Predicted)

2-naphthalen-1-ylpropan-2-ol Usage And Synthesis

Synthesis

To a stirred solution of dry THF (400 mL) of 1-bromonaphthalene (12, 41.41 g, 0.2 mol) held at -78 °C under N2 atmosphere, a hexane solution (125 mL, 0.2 mol) of 1.6 M n-BuLi was slowly added dropwise via syringe. After the dropwise addition, the resulting solution was continued to be stirred at -78 °C for 1 hour. Subsequently, dry acetone (17.42 g, 0.3 mol) was added dropwise via syringe to the reaction system. The reaction mixture was stirred at -78 °C for 0.5 h. After that, it was brought to room temperature and stirring was continued for 1 h. The reaction mixture was then stirred at -78 °C for 0.5 h. The reaction mixture was slowly poured into ice water (2 L), stirred and extracted with CH2Cl2 (500 mL × 3). The organic phases were combined, washed with 5% brine (500 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product. The crude product was purified by column chromatography and then milled with n-hexane/EtOAc (1:100, v/v) to obtain the pure 2-(naphthalen-1-yl)-2-propanol (13) as colorless needle-like crystals (33.90 g, 91%). Melting point: 88.5-90°C (literature value: 83-85°C [18]).1H NMR (DMSO-d6, 400 MHz) δ: 8.84-8.87 (m, 1H), 7.87-7.90 (m, 1H), 7.78 (d, 1H, J = 8.0 Hz), 7.56 (dd, 1H, J = 0.8, 7.6 Hz), 7.43-7.49 (m, 2H), 7.40 (t, 1H, J = 7.8 Hz), 5.24 (s, 1H), 1.70 (s, 6H).

References

[1] Medicinal Chemistry, 2017, vol. 13, # 3, p. 260 - 281
[2] Journal of Organic Chemistry, 2014, vol. 79, # 17, p. 8348 - 8357
[3] Journal fuer Praktische Chemie (Leipzig), 1987, vol. 329, # 3, p. 439 - 446

2-naphthalen-1-ylpropan-2-ol(6301-54-8)Related Product Information

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• α,α-Dimethyl-4-(1-methylethoxy)benzenemethanol
• 2-(2-methylsulfanylphenyl)propan-2-ol
• α,α-Dimethyl-2-(methylthio)-3-pyridinemethanol
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• α,α-Dimethyl-2-(1-pyrrolidinyl)-3-pyridinemethanol
• 2-(Thiophen-2-yl)propan-2-ol
• 2-(2-propan-2-ylphenyl)propan-2-ol
• α,α-Diethyl-4-propoxybenzenemethanol
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• α,α-Dimethyl-5-(1-methylethoxy)-3-pyridinemethanol
• α,α-Diethyl-5-methoxy-2-methylbenzenemethanol
• 3-(6-methoxynaphthalen-2-yl)pentan-3-ol
• 3-(5-fluoro-2-methylphenyl)pentan-3-ol
• 2-(4-methylsulfanylphenyl)propan-2-ol
• 2-(3-methylsulfanylphenyl)propan-2-ol
• 2-(4-propylphenyl)propan-2-ol
• 3-(4-propylphenyl)pentan-3-ol