ChemicalBook CAS DataBase List 8-(Benzyloxy)-8-oxooctanoic acid

8-(Benzyloxy)-8-oxooctanoic acid synthesis

5synthesis methods

Product Name: 8-(Benzyloxy)-8-oxooctanoic acid
CAS Number:15570-39-5
Molecular formula:C15H20O4
Molecular Weight:264.32

To a solution of octanedioic acid (1 g, 5.7 mmol) and benzylic alcohol (0.31 g, 2.9 mmol) in dichloromethane (25 mL) were added 4-dimethylaminopyridine (0.39 g, 3.2 mmol) and N,N'-dicyclohexylcarbodiimide (0.66 g, 3.2 mmol). The mixture was stirred at room temperature for 1 h and concentratedin vacuo. Water (40 mL) was then added and the mixture was extracted with ethyl acetate (3 x 40 mL). The combined organic layers were washed with water (2 x 75 mL) and concentratedin vacuo. The obtained crude product was purifiedviasilica gelcolumn chromatography (cyclohexane/ethyl acetate, 80/20) affording 8-(Benzyloxy)-8-oxooctanoic acid as a translucent solid (0.545 g, 71% yield).

505-48-6 Synthesis

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100-51-6 Synthesis

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Yield:15570-39-5 71%

Reaction Conditions:

with dmap;dicyclohexyl-carbodiimide in dichloromethane at 20; for 1 h;Steglich Esterification;

Steps:

8-(Benzyloxy)-8-oxooctanoic acid(1)

To a solution of octanedioic acid (1 g, 5.7 mmol) and benzylic alcohol (0.31 g, 2.9 mmol) in dichloromethane (25 mL) were added 4-dimethylaminopyridine (0.39 g, 3.2 mmol) andN,N'-dicyclohexylcarbodiimide (0.66 g, 3.2 mmol). The mixture was stirred at room temperature for 1 h and concentratedin vacuo. Water (40 mL) was then added and the mixture was extracted with ethyl acetate (3 x 40 mL). The combined organic layers were washed with water (2 x 75 mL) and concentratedin vacuo. The obtained crude product was purifiedviasilica gelcolumn chromatography (cyclohexane/ethyl acetate, 80/20) affording1as a translucent solid (0.545 g, 71% yield).¹H NMR (CDCl₃, 300 MHz) δ 7.39-7.30 (m, 5H), 5.11 (s, 2H), 2.38-2.31 (m, 4H), 1.70-1.58 (m, 4H), 1.37-1.31 (m, 4H).¹³C NMR (CDCl₃, 75 MHz) δ 178.9 (Cq), 173.7 (Cq), 136.2 (Cq), 128.7 (2 CH), 128.3 (3 CH), 66.3 (CH₂), 34.4 (CH₂), 33.9 (CH₂), 28.8 (CH₂), 28.8 (CH₂), 24.9 (CH₂), 24.6 (CH₂). LR-MS (DCI/NH₃) m/z calculated for C₁₅H₂₁O₄(M+H⁺)265.15, found 265.2 (M+H⁺), 282.2 (M+NH₄⁺).

References:

Ouji, Manel;Nguyen, Michel;Mustière, Romain;Jimenez, Tony;Augereau, Jean-Michel;Benoit-Vical, Fran?oise;Deraeve, Céline [Bioorganic and Medicinal Chemistry Letters,2021,vol. 39,art. no. 127884] Location in patent:supporting information

505-48-6 Synthesis

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