1,3-Diethyl 2-(3-oxocyclohexyl)propanedioate → 2-(3-Oxocyclohexyl)acetic acid

Reaction equation

C([O:3][C:4](=[O:18])[CH:5]([CH:11]1[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[CH2:12]1)C(OCC)=O)C.O=C1C(CCC)CCC(CC(O)=O)C1>>[O:17]=[C:13]1[CH2:14][CH2:15][CH2:16][CH:11]([CH2:5][C:4]([OH:18])=[O:3])[CH2:12]1

Participants

Reactant 2

HCID 3170491,3-Diethyl 2-(3-oxocyclohexyl)propanedioate

HCID 11344629(3-Oxo-4-propyl-cyclohexyl)-acetic acid

Product 1

HCID 37268152-(3-Oxocyclohexyl)acetic acidYield 70%

Procedure

Step 2 (3-Oxo-cyclohexyl)-acetic acid was prepared in 70% yield from 2-(3-oxo-cyclohexyl)-malonic acid diethyl ester by the method described above for the synthesis of (3-oxo-4-propyl-cyclohexyl)-acetic acid: 1H NMR (300 MHz, CDCl3) δ 2.58-1.92 (m, 7H), 1.80-1.61 (m, 1H), 1.52-1.42 (m, 1H); ESI MS m/z 155 [M−H]−.

Sources & evidence

ORD record: ord-3346feb220d5492e86e1e6daff9547a3
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07727997B2

Reaction notes

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