Dodecanedioic Acid → Methyl 2-(3-oxocyclopentyl)acetate

HRID 1093093Notes

Reaction equation

[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([CH:7](C(OC)=O)[C:8]([O:10][CH3:11])=[O:9])[CH2:3]1.C(O)(=O)CCCCCCCCCCC(O)=O>>[O:1]=[C:2]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([O:10][CH3:11])=[O:9])[CH2:3]1

Participants

Reactant 2

HCID 12736Dodecanedioic Acid

HCID 11608197Dimethyl 2-(3-oxocyclopentyl)malonate

Product 1

HCID 11355614Methyl 2-(3-oxocyclopentyl)acetateYield 71%

Conditions

Temperature: 210 °C

Procedure

A 1000 mL flask was charged with dimethyl 2-(3-oxocyclopentyl)malonate (329.1 g, 1536 mmol), and dodecanedioic acid (283 g, 1229 mmol). The mixture was heated (210° C., oil bath) under a nitrogen atmosphere for 20 hrs, then distilled (˜1 torr, 180° C. oil bath) to give the title compound (170.4 g, 1091 mmol, 71.0% yield) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ ppm 3.68 (3 H, s), 2.55-2.66 (1 H, m), 2.40-2.51 (3 H, m), 2.27-2.35 (1 H, m), 2.13-2.26 (2 H, m), 1.87 (1 H, ddd, J=18.23, 10.30, 1.37 Hz), 1.53-1.63 (1 H, m). 13C NMR (126 MHz, CDCl3) δ ppm 218.36, 172.58, 51.78, 44.70, 39.53, 38.40, 33.52, 29.31.

Workup

distillationdistilled (˜1 torr, 180° C. oil bath)

Sources & evidence

ORD record: ord-e07d20f0b0464243a5cc9c09efab9ed3
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129398B2

Reaction notes

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