ChemicalBook CAS DataBase List METHYL 4-FORMYL-1-NAPHTHOATE

METHYL 4-FORMYL-1-NAPHTHOATE synthesis

11synthesis methods

Product Name:METHYL 4-FORMYL-1-NAPHTHOATE
CAS Number:62855-40-7
Molecular formula:C13H10O3
Molecular Weight:214.22

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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62855-40-7
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Yield: 80%

Reaction Conditions:

with ozone in methanol;dichloromethane at -78;

Steps:

3
Preparation 3: methyl 4-formyl-1-naphthoate A solution of (E)-methyl 4-styryl-1-naphthoate (Preparation 2, 1.31 g, 2.0 mmol) in 3:1 CH₂Cl₂/MeOH (40 mL) was cooled to -78° C. Sample was subjected to ozonylysis for 10 minutes until blue color was noted. Reaction was quenched with dimethyl sulfide (400 μL) and allowed to warm to room temperature. The residue was purified by chromatography on silica gel eluting from 100% heptane to 50:50 EtOAc:heptane to afford a solid (0.78 g, 80%). ¹H NMR (CDCl₃) δ ppm: 10.52 (1H), 9.28 (1H), 8.83 (1H), 8.22 (1H), 8.04 (1H), 7.79-7.70 (2H), 4.08 (3H).

References:

PFIZER INC. US2012/77765, 2012, A1 Location in patent:Page/Page column 15