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 1960036Notes

Reaction equation

HRID 1960036 reaction equation
[CH2:1]([O:3][C:4]([CH:6]=[C:7]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH2:9][CH2:8]1)=[O:5])[CH3:2]>CCOC(C)=O.CO.[Pd]>[CH2:1]([O:3][C:4]([CH2:6][CH:7]1[CH2:16][CH2:15][C:10]2([O:11][CH2:12][CH2:13][O:14]2)[CH2:9][CH2:8]1)=[O:5])[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)acetate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

A suspension of 8-ethoxycarbonylmethylidene-1,4-dioxaspiro[4.5]decane (crude, 172.9 g) 10% Pd—C (53.2% wet, 6.5 g) in EtOAc/MeOH (1250 mL and 400 mL) is stirred under H2 atmosphere at room temperature for 4 hours. The reaction mixture is filtered, and the filtrate is concentrated in vacuo to afford crude 8-ethoxycarbonylmethyl-1,4-dioxaspiro[4.5]decane. The crude product is used without further purification.

Workup

  1. filtrationThe reaction mixture is filtered
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-adc1cb42605841d6974ea6b40796c379
Source dataset
uspto-grants-2013_04
Patent number
US08410275B2

Reaction notes

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