8-(Benzyloxy)-8-oxooctanoic acid Chemical Properties

Melting point:

34.5-35 °C

Boiling point:

195-197 °C(Press: 1.1 Torr)

Density 

1.120±0.06 g/cm3(Predicted)

pka

4.76±0.10(Predicted)

InChI

InChI=1S/C15H20O4/c16-14(17)10-6-1-2-7-11-15(18)19-12-13-8-4-3-5-9-13/h3-5,8-9H,1-2,6-7,10-12H2,(H,16,17)

InChIKey

KIDAZJWBHFODTB-UHFFFAOYSA-N

SMILES

C(OCC1=CC=CC=C1)(=O)CCCCCCC(O)=O

8-(Benzyloxy)-8-oxooctanoic acid Usage And Synthesis

Synthesis

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).