ChemicalBook CAS DataBase List 9-Anthracenemethanol

9-Anthracenemethanol synthesis

12synthesis methods

Product Name:9-Anthracenemethanol
CAS Number:1468-95-7
Molecular formula:C15H12O
Molecular Weight:208.26

9-Anthracenemethanol is synthesized by hydrogenation of 9-anthracenecarboxaldehyde. It is a versatile precursor to supramolecular assemblies.

642-31-9 Synthesis

642-31-9
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$10.00/5g

1468-95-7
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$8.00/5g

Yield:1468-95-7 99%

Reaction Conditions:

with sodium tetrahydroborate in ethanol at 20; for 0.5 h;

Steps:

Anthracen-9-yl-methanol

General procedure: 9-Anthraldehyde (1; 206 mg, 1.0 mmol) wassuspended in ethanol (3.0 mL). To the suspension was added sodium borohydride(38 mg, 1.0 mmol). After stirring for 30 min at rt, the reaction mixture was quenched with water (2 mL). The aqueous phase was extracted with ether (5 mL). The organicextract was dried over anhydrous Na2SO4 and concentrated to give the crude alcohol, which waspurified by flash column chromatography (silica gel 10 g, hexanes/ethyl acetate = 80/20) to give thealcohol 5 (206 mg, 99%) as a pale yellow solid. Registry number 1468-95-7; Rf = 0.27(hexane:AcOEt = 80:20); 1H NMR (CDCl3, 300 MHz) δ = 1.80 (brs, 1H, -OH), 5.62 (s, 2H, -CH2-),7.38-7.64 (m, 4H, Ar), 8.00 (d, J = 8.3 Hz, 2H, Ar), 8.38 (d, J = 8.7 Hz, 2H, Ar), 8.44 (s, 1H, H-10)

References:

Mase, Nobuyuki;Takabe, Kunihiko;Tanaka, Fujie [Tetrahedron Letters,2013,vol. 54,# 32,p. 4306 - 4308] Location in patent:supporting information