ChemicalBook CAS DataBase List 5-Chloro-1-tetralone

5-Chloro-1-tetralone synthesis

11synthesis methods

Product Name:5-Chloro-1-tetralone
CAS Number:26673-30-3
Molecular formula:C10H9ClO
Molecular Weight:180.63

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26673-30-3
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Yield: 62%

Reaction Conditions:

Stage #1:5-amino-3,4-dihydronaphthalen-1(2H)-one with hydrogenchloride;sodium nitrite in ethanol;water at 0; for 0.25 h;
Stage #2: with copper(l) chloride in ethanol;water at 95; for 0.25 h;

Steps:

6.3 6.3. Synthesis of 5-chloro-3,4-dihydronaphthalen-l(2H)-one
5-amino-3,4-dihydronaphthalen-l(2H)-one (1 g, 6.2 mmol) in HCl (36%, 2 mL) and EtOH (8 mL) at 0 °C was treated with an aqueous solution of NaN0₂ (0.582 g, 8.4 mmol in 1 mL water for 15 min. This mixture was added to a solution of CuCl (0.3 g, 3.1 mmol) in HCl (36%, 10 mL) at 95 °C and kept at this temperature for 15 min. The solution was cooled down to room temperature, diluted with water, and extracted with EtOAc. The organic phase was collected, washed with sat. NaHCC , dried over MgSC , and purified by column chromatography with 40-50% EtOAc:Hex on silica gel. Desired compound was afforded. (0.7 g, 62%). NMR (400 MHz, chloroform-d) δ 7.53 (dd, / = 7.8, 1.2 Hz, 1H), 7.14 (tt, / = 7.8, 0.7 Hz, 1H), 6.88 (dd, / = 7.8, 1.2 Hz, 1H), 3.70 (s, 2H), 2.69 (t, / = 6.2 Hz, 2H), 2.66 - 2.60 (m, 2H), 2.30 - 2.07 (m, 2H).

References:

THE BOARD OF REGENTS OF THE UNIVERSITY OF TEXAS SYSTEM;GAO, Jinming;LUI, Yuliang;WEI, Qi;MA, Xinpeng;HUANG, Gang WO2017/106624, 2017, A1 Location in patent:Paragraph 00141

68449-31-0 Synthesis