[ CAS No. 3453-33-6 ] 6-Methoxy-2-Naphthaldehyde

Cat. No.: A131663

2D 3D

Structure of 3453-33-6 * Storage: Inert atmosphere,Room Temperature

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* Storage: Inert atmosphere,Room Temperature

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Quality Control of [ 3453-33-6 ]

COA NMR CNMR HPLC LC-MS

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Specification

Alternatived Products of [ 3453-33-6 ]

Product Details of [ 3453-33-6 ]

CAS No. :	3453-33-6	MDL No. :	MFCD00081152
Formula :	C₁₂H₁₀O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VZBLASFLFFMMCM-UHFFFAOYSA-N
M.W :	186.21	Pubchem ID :	76991
Synonyms :		Chemical Name :	6-Methoxy-2-naphthaldehyde

Safety of [ 3453-33-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3453-33-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 3453-33-6 ]

[ 3453-33-6 ] Synthesis Path-Downstream 1~1

1
[ 3453-33-6 ]
[ 2605-68-7 ]
[ 178552-34-6 ]

Yield	Reaction Conditions	Operation in experiment
	In xylenes; at 170℃; for 4h;Heating / reflux;	EXAMPLE 7; To a xylenes solution of 6-methoxy-2-naphthaldehyde (0.855g, 4.585 mmol) was added the stabilized ylide shown in Scheme 2 (2.16g, 5.96 mmol, 1.3 eq.) at room temperature. The solution was heated to reflux for 4 h. The solvent was removed under vacuum, and the residue was chromatographed with AcOEt/Hexanes (4 to 1) to obtain the ethyl enoate intermediate. To a methanol solution of this intermediate (5.73 g) was added Pd/C (0-3 g), and the mixture was subjected to <n="33"/>hydrogenation under a balloon atmosphere of H2 gas, at room temperature for 16 h. The solution was filtered, and the solvent was removed in vacuo to obtain the saturated ester. The methoxy naphthyl ester (5.73 g) was treated with NCS (0.82g, 6.11 mmol, 1.1 eq) in DMF solvent at room temperature, and the solution was stirred for 16 h. Removal of the DMF in vacuo provided a residue which was recrystalized from methanol/methylene chloride to obtain the chlorinated intermediate. The racemic mixture of this chloride (1.5 g, 3.69 mmol) was separated into its single enantiomers using chiral HPLC with a Chiralcel OJ column, and isocratic elution with 35% isopropanol-heptane. The ethyl ester intermediate (65 mg, 0.21 mmol) was dissolved in (1:1) acetic acid-HCl (2 mL) and heated to 110 0C for 10 min. Then 5 mL of water was added, and the solution cooled to 0 0C to obtain the acid intermediate after filtration. Oxalyl chloride (0.3 mmol) was then added to a CH2CI2 (2 mL) solution of this acid intermediate (45 mg, 0.1 mmol), and one drop of DMF was added at 0 0C. The solvent was removed in vacuo after the solution was sirred for 1 h at room temperature. The residue was dissolved in THF (2 mL), and this solution was added to a THF (2 mL) solution of 3-amino-2-carboxylthiophene (0.11 mmol) and Et3N (0.3 mmol) at 0 0C. The pure thiophene methyl ester intermediate was obtained after HPLC purification. Potassium trimethylsilanolate (4 eq, 0.4 mmol) was added to a THF solution of this methyl ester intermediate (0.09 mmol) at 0 0C. The solution was stirred at room temperature for 2 h, and the desired product was obtained by preparative RPHPLC purification. 1H NMR (CD3OD, 500 MHz) δ 8.07 (d, IH), 7.99 (d, IH), 7.74 (d,lH), 7.66 (s, IH), 7.64(d, IH), 7.47 (dd IH), 7.40(d, IH), 4.00 (s, 3H), 3.17(m, IH), 2.97 (m, 2H), 1.30 (d, 3H); LCMS m/z 402 (M-I).

Reference： [1]Patent: WO2007/120575,2007,A2 .Location in patent: Page/Page column 23; 30-31

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Technical Information

• Barbier Coupling Reaction • Baylis-Hillman Reaction • Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Bucherer-Bergs Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Chaykovsky Reaction • Corey-Fuchs Reaction • Fischer Indole Synthesis • Friedel-Crafts Reaction • Grignard Reaction • Hantzsch Dihydropyridine Synthesis • Henry Nitroaldol Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Hydrogenolysis of Benzyl Ether • Julia-Kocienski Olefination • Knoevenagel Condensation • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Mukaiyama Aldol Reaction • Nomenclature of Ethers • Nozaki-Hiyama-Kishi Reaction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Ethers • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Ethers • Reformatsky Reaction • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Stetter Reaction • Stobbe Condensation • Tebbe Olefination • Ugi Reaction • Vilsmeier-Haack Reaction • Wittig Reaction • Wolff-Kishner Reduction

Historical Records

Related Functional Groups of
[ 3453-33-6 ]

Aryls

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Aldehydes

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3-Methoxy-5-methylbenzaldehyde

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4-Methoxy-2,6-dimethylbenzaldehyde

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[ CAS No. 3453-33-6 ] 6-Methoxy-2-Naphthaldehyde

Quality Control of [ 3453-33-6 ]

Related Doc. of [ 3453-33-6 ]

Product Details of [ 3453-33-6 ]

Safety of [ 3453-33-6 ]

Application In Synthesis of [ 3453-33-6 ]

[ 3453-33-6 ] Synthesis Path-Downstream 1~1

Technical Information

Related Functional Groups of [ 3453-33-6 ]

Aryls

Aldehydes

Ethers

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 3453-33-6 ]