ChemicalBook CAS DataBase List ADIPIC SEMIALDEHYDE METHYL ESTER

ADIPIC SEMIALDEHYDE METHYL ESTER synthesis

13synthesis methods

Product Name:ADIPIC SEMIALDEHYDE METHYL ESTER
CAS Number:6654-36-0
Molecular formula:C7H12O3
Molecular Weight:144.17

4547-43-7 Synthesis

4547-43-7
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$19.00/100mg

6654-36-0
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$20.00/250mg

Yield: 100%

Reaction Conditions:

with pyridinium chlorochromate in dichloromethane at 20; for 2.5 h;

Steps:

2
PCC (2.65 g, 12.3 mmoles) was added to a solution of methyl 6-hydroxyhexanoate (4) (1.2 g, 8.19 mmoles) in CH₂Cl₂ (50 ml). The mixture was stirred at room temperature for 2.5 hours. After that time, the solvent was removed under reduced pressure. The residue was suspended in a 1:1 hexane/AcOEt mixture (30 ml) and filtered through silica gel to remove the remains of the reagent, obtaining (1.16 g, quantitative yield) methyl 5-formylpentanoate (5), which was used in the following step without purifying. ¹H-NMR (200MHz, CDCl₃). δ 9.71 (1H, m, H-6), 3.61 (3H, s, -OCH₃), 2.39 (4H, m, H-2, H-5), 1.65 (4H, m, H-3, H-4).

References:

Consejo Superior de Investigaciones Cientificas EP2287146, 2011, A1 Location in patent:Page/Page column 16