ChemicalBook CAS DataBase List 6-Chloro-1-tetralone

6-Chloro-1-tetralone synthesis

9synthesis methods

Product Name:6-Chloro-1-tetralone
CAS Number:26673-31-4
Molecular formula:C10H9ClO
Molecular Weight:180.63

A solution of sodium nitrite (173 mg, 2.51 mmol) in water (5 mL) at 0 °C (ice-bath) was added to a magnetically stirred suspension of 6-Amino-1-tetralone (360 mg, 2.23 mmol) in aqueous hydrochloric acid (10 mL, 6 M) at 0 °C. This reaction mixture was added dropwise to a solution of copper(I) chloride (267 mg, 2.70 mmol) in concentrated hydrochloric acid (5 mL) at 0 °C. It was allowed to warm up to room 100 temperature and stirred for a further 2 h after which it was neutralised with solid sodium carbonate, extracted with ethyl acetate (3 × 20 mL) and concentrated in vacuo to give slightly yellow oil. This material was subjected to flash chromatography (50% chloroform in hexane) and concentration of the appropriate fractions afforded 6-chloro-1-tetralone (180 mg, 45%) as a waxy solid.

3470-53-9 Synthesis

3470-53-9
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26673-31-4
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Yield:26673-31-4 88%

Reaction Conditions:

with tert.-butylnitrite;copper dichloride in acetonitrile at 60; for 0.75 h;

Steps:

13.a Step a⁴

CuCl₂(2.0 g, 15.0 mmol) and t-butyl nitrite (2.2 mL, 15.0 mmol) in dry CH₃CN were heated at 60° C., followed by the addition of 6-aminotetralone (2.0 g, 12.0 mmol). The reaction mixture was heated for 45 min, then cooled down at room temperature, quenched with 2N HCl (200 mL) and Et₂O (200 mL). The aqueous layer was extracted with Et₂O and the combined organic layer was washed with water, brine, dried over anhydrous Na₂SO₄, concentrated by rotary evaporation, and purified by column chromatography to give 6-chloro-3,4-dihydronaphthalen-1(2H)-one (16) (88%). 111 NMR (600 MHz, CDCl₃) δ 7.96 (d, J=6.0 Hz, 1H), 7.28-7.26 (m, 2H), 2.94 (t, J=6.0 Hz, 2H), 2.65 (t, J=6.0 Hz, 2H), 2.16-2.11 (m, 2H), 7.12-7.07 (m, 2H), 6.92 (d, J=12.0 Hz, 1H), 6.85 (s, 1H), 5.67 (s, 1H). GC-MS (ES) for C₁₀H₉C10 [M]⁺180.

References:

US2015/105351,2015,A1 Location in patent:Paragraph 0440

29480-09-9
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26673-31-4
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22991-05-5 Synthesis

22991-05-5
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26673-31-4
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References

Methanesulfonic acid, 1,1,1-trifluoro-, 5,6,7,8-tetrahydro-5-oxo-2-naphthalenyl ester

144464-64-2
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26673-31-4
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Benzenebutanoic acid, 3-chloro-, ethyl ester

1355061-67-4
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26673-31-4
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References

6-Chloro-1-tetralone Related Search:

Chlormezanone Dihydromyrcenol Epichlorohydrin Nabumetone Decahydronaphthalene 1-Tetralone 5-Chloro-2-tetralone 7-Chloro-1-tetralone 5-Chloro-1-tetralone