Sodium Hydroxide → 5-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylic acid

HRID 2110980

Reaktionsgleichung

Reaktionsgleichung von HRID 2110980
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]1[CH:13]([C:14]([O:16]CC)=[O:15])[CH:8]1[CH2:7][CH2:6]2.[OH-].[Na+]>CO.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]1[CH:13]([C:14]([OH:16])=[O:15])[CH:8]1[CH2:7][CH2:6]2

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 23001093ethyl 5-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylate

Produkt 1

HCID 230011155-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

Ethyl 5-methoxy-1a,2,3,7b-tetrahydro-1H-cyclopropa[a]naphthalene-1-carboxylate (0.2 g, 0.8 mmol) was dissolved in 2 ml of methanol and the solution of sodium hydroxide (0.2 g, 50 mmol) in 2 ml of water was added to the reaction mixture and stirred at ambient temperature overnight. The extraction of basic reaction mixture into hexane showed that no starting material present. The reaction mixture was acidified with excess of 3M HCl solution (pH=1), and extracted into ethylacetate (3×15 ml). The combined extracts were washed with water and brine, dried over Na2SO4 and concentrated by rotary evaporation to give 0.1 5 g of mixture of cis/trans acids as white solid.

Aufarbeitung

  1. extractionThe extraction of basic reaction mixture into hexane
  2. extractionextracted into ethylacetate (3×15 ml)
  3. washThe combined extracts were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated by rotary evaporation
  6. customto give

Quellen und Nachweise

ORD-Eintrag
ord-5382b37635ab43cfba08a59638a68373
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07517992B2

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