1,2,3,4-tetrahydronaphthalen-1-ylmethanol synthesis

12synthesis methods

Product Name:1,2,3,4-tetrahydronaphthalen-1-ylmethanol
CAS Number:66377-63-7
Molecular formula:C11H14O
Molecular Weight:162.23

1914-65-4
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1,2,3,4-tetrahydronaphthalen-1-ylmethanol

66377-63-7
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Yield:66377-63-7 97%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20; for 1 h;

Steps:

2-2 <2-2> Preparation of (1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol

<2-2> Preparation of (1,2,3,4-tetrahydro-naphthalen-1-yl)-methanol
200 mg (1.10 mmol) of 1,2,3,4-tetrahydro-naphthalen-1-carboxylic acid compound was dissolved in 9 mL of tetrahydrofuran, and then 129 mg (3.30 mmol) of lithium aluminum hydride was added at 0° C. and stirred at room temperature for 1 hour.
Water was slowly added to quench the reaction, and when a gel was formed by adding ethyl acetate, the celite was filtered.
Then, the residue was dissolved again in 20 mL of ethyl acetate and the organic layer was washed with distilled water three times.
The organic layer was dried with anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure to give 180 mg of colorless oil (yield: 97%).
¹H-NMR (300 MHz, CDCl₃) δ 1.69-1.98 (m, 4H), 2.74-2.78 (m, 2H), 2.94-3.01 (m, 1H), 3.80 (d, 2H, J=8.3 Hz), 7.07-7.24 (m, 4H)

References:

US2013/11417,2013,A1 Location in patent:Paragraph 0092; 0093; 0094; 0095

2510-03-4 Synthesis