Citric Acid → 8-Ethyl-1,4-dioxaspiro[4,4]nonane-7-carboxylic acid

HRID 1969896Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969896
[CH2:1]([CH:3]1[CH2:11][C:6]2([O:10][CH2:9][CH2:8][O:7]2)[CH2:5][CH:4]1[C:12]([O:14]CC)=[O:13])[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH2:1]([CH:3]1[CH2:11][C:6]2([O:7][CH2:8][CH2:9][O:10]2)[CH2:5][CH:4]1[C:12]([OH:14])=[O:13])[CH3:2]

Komponenten

5

Edukt 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 58557462Ethyl 8-ethyl-1,4-dioxaspiro[4,4]nonane-7-carboxylate

Produkt 1

HCID 585573038-Ethyl-1,4-dioxaspiro[4,4]nonane-7-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A round bottom flask was charged with ethyl 8-ethyl-1,4-dioxaspiro[4.4]nonane-7-carboxylate (0.32 g, 1.4 mmol) and aqueous sodium hydroxide (1 N, 14.0 mL, 14.0 mmol). The solution was stirred overnight at rt. To the solution was added DCM (30 mL) followed by the addition of 20% aqueous citric acid (about 20 mL) to reach pH of about 2. The layers were separated and the aqueous solution was extracted with DCM (2×30 mL) and DCM/EtOAc (1:1, 30 mL). The combined extracts were dried over anhydrous MgSO4, filtered, and concd under reduced pressure to give 8-ethyl-1,4-dioxaspiro[4.4]nonane-7-carboxylic acid as a clear, colorless oil (0.27 g, 96%): LC/MS (Table 1, Method c) Rt=1.20 min; MS m/z: 201 (M+H)+.

Aufarbeitung

  1. customThe layers were separated
  2. extractionthe aqueous solution was extracted with DCM (2×30 mL) and DCM/EtOAc (1:1, 30 mL)
  3. dry with materialThe combined extracts were dried over anhydrous MgSO4
  4. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-14ee3734f31949289f06eae7c604274f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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