Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl ester → Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetate

HRID 420765

Reaction equation

HRID 420765 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH:5]=[C:6]1[CH2:15][CH2:14][C:9]2([O:13][CH2:12][CH2:11][O:10]2)[CH2:8][CH2:7]1)[CH3:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH:6]1[CH2:15][CH2:14][C:9]2([O:10][CH2:11][CH2:12][O:13]2)[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 1

HCID 373318Acetic acid, 2-(1,4-dioxaspiro(4.5)dec-8-ylidene)-, ethyl ester

Product 1

HCID 15700391Ethyl 2-(1,4-dioxaspiro[4.5]decan-8-yl)acetateYield 97.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

(1,4-Dioxa-spiro[4.5]dec-8-ylidene)-acetic acid ethyl ester (1.10 g, 4.86 mmol) was dissolved in 30 ml ethyl acetate and stirred with 110 mg Pd/C 10% under hydrogen atmosphere for 4 hours. The catalyst was filtered off and the solvent evaporated. The crude product (1.08 g, 97%) [MS: m/e=229.3 (M+H+)] was obtained as a colourless liquid and used without any further purification for the next step.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-4d0a63cc5ae84bf2b5b3b977b0a4b14d
Source dataset
uspto-grants-2012_01
Patent number
US08097637B2

Linked notes

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