7-Methoxy-1-naphthaleneethanol synthesis
- Product Name:7-Methoxy-1-naphthaleneethanol
- CAS Number:99416-99-6
- Molecular formula:C13H14O2
- Molecular Weight:202.25
176727-95-0
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Yield:99416-99-6 98%
Reaction Conditions:
Stage #1: 2-(2-methoxynaphthalen-8-yl)acetaldehydewith sodium tetrahydroborate;ethanol at 20; for 2 h;
Stage #2: with hydrogenchloride in water;ethyl acetate; for 0.5 h;
Steps:
11.C Step C: 2-(7-methoxynaphthalen-1 -yl)ethanol
Sodium borohydride (38 mg; 1 mmol) is added to a solution of the product of Step B above (20 mg; 0.1 mmol) in ethanol (1 mE). Afier stirring for 2 hours at ambient temperature, the mixture is hydrolysed with 2M aqueous HC1 solution (2 mE) and is then stirred for 30 minutes in the presence of ethyl acetate (1 mE). The solution is extracted 4 times with ethyl acetate. The organic fractions are combined, dried over sodium sulphate and filtered. Afier evaporating off the solvent, the crude product is purified by chromatography on a silica gel colunm (eluant: ethyl acetate/petroleum ether 20/80) to yield the title product in the form of a white solid (19.8 mg; 98%).‘H NMR spectroscopic analysis (CDC13, 300.13 MHz, ? in ppm): 7.72 (d, J=9.1 Hz, 1H); 7.63 (d, J=8.1 Hz, 1H); 7.3-7.21 (m, 3H); 7.13 (dd, J=9.1 and 2.6 Hz, 1H); 3.93 (t, J=6.7 Hz, 2H); 3.88 (s, 3H); 3.24 (d, J=6.7 Hz, 2H); 1.99 (bs, 1H). ‘3C NMR spectroscopic analysis (CDC13, 75.5 MHz, ? in ppm): 157.8 (s); 133.2 (s); 133.0 (s); 130.4 (d); 129.4 (s); 127.7 (d); 127.1 (d); 123.3 (d); 118.1 (d); 102.5 (d); 62.7 (0; 55.4 (q); 36.4 (t). Mass spectrometry (ESI; mlz (%D: 202 (29) [M]’;171 (100).
References:
US2016/368859,2016,A1 Location in patent:Paragraph 0199; 0200; 0201; 0202
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