6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

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CAS:32263-70-0
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6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one Basic information
Product Name:6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one
Synonyms:6-(Benzyloxy)-3,4-dihydro-1(2H)-naphthalenone;6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one;1(2H)-Naphthalenone, 3,4-dihydro-6-(phenylMethoxy)-;6-Benzyloxy-3,4-dihydro-2H-naphthalen-1-one;oxy)-3,4-dihydronaphthaL;6-phenylmethoxy-3,4-dihydro-2H-naphthalen-1-one;6-(benzyloxy)-1,2,3,4-tetrahydronaphthalen-1-one;6-benzyloxytetralone
CAS:32263-70-0
MF:C17H16O2
MW:252.31
EINECS:
Product Categories:
Mol File:32263-70-0.mol
6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one Structure
6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one Chemical Properties
Melting point 96-99 °C(Solv: cyclohexane (110-82-7))
Boiling point 433.4±34.0 °C(Predicted)
density 1.160±0.06 g/cm3(Predicted)
storage temp. Sealed in dry,Room Temperature
AppearanceLight brown to brown Solid
InChIInChI=1S/C17H16O2/c18-17-8-4-7-14-11-15(9-10-16(14)17)19-12-13-5-2-1-3-6-13/h1-3,5-6,9-11H,4,7-8,12H2
InChIKeySAYPPJQQGVXKAP-UHFFFAOYSA-N
SMILESC1(=O)C2=C(C=C(OCC3=CC=CC=C3)C=C2)CCC1
Safety Information
MSDS Information
6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one Usage And Synthesis
Synthesis
6-Hydroxy-1-tetralone

3470-50-6

Benzyl bromide

100-39-0

6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one

32263-70-0

General procedure: 6-hydroxy-1-tetralone (0.3 g, 1.85 mmol) was suspended in acetone (15 mL) containing K2CO3 (3.70 mmol). Benzyl bromide (2.035 mmol) was added to the reaction mixture and heated under reflux conditions for 6 hours. The reaction process was monitored by silica gel thin layer chromatography (TLC) using ethyl acetate with petroleum ether (1:2) as mobile phase. Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad and the filtrate was subsequently concentrated under vacuum. The resulting crude product was purified by recrystallization from cyclohexane to give 6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one.

References[1] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2758 - 2763
[2] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 12, p. 2758 - 2763
[3] Patent: US2018/155322, 2018, A1. Location in patent: Paragraph 1502; 1503
[4] European Journal of Organic Chemistry, 2003, # 15, p. 2799 - 2812
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 1, p. 144 - 148
6-(benzyloxy)-3,4-dihydronaphthalen-1(2H)-one Preparation Products And Raw materials
Raw materials6-(benzyloxy)-2,3-dihydroinden-1-one-->6-Hydroxy-1-tetralone-->Benzyl chloride-->Potassium carbonate-->6-methoxy-1-tetralone-->Benzyl bromide-->Acetone
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