Reaktion #709255

Reaktionsgleichung

1,2-dichloro-3-hydroxy-8-oxo-5a-propyl-5a,6,7,8-tetrahydrodibenzofuran

ethyl bromoacetate

→

(1,2-dichloro-8-oxo-5a-propyl-5a,6,7,8-tetrahydrodibenzofuran-3-yl)acetic acid

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe solid ester which precipitated
2. 2
   Sonstigewas removed by filtration
3. 3
   workup.DISSOLUTIONthen dissolved in methanol (15 ml)
4. 4
   workup.ADDITIONcontaining water (1 ml) and 10N sodium hydroxide (1 ml)
5. 5
   workup.ADDITIONAfter 1/2 hour the methanol solution was poured into dilute aqueous hydrochloric acid
6. 6
   Extraktionextracted with ether which
7. 7
   Waschenwas washed with water, brine
8. 8
   Trocknendried over MgSO4
9. 9
   Sonstigeevaporated in vacuo

Vorschrift

A stirred mixture of 1,2-dichloro-3-hydroxy-8-oxo-5a-propyl-5a,6,7,8-tetrahydrodibenzofuran (0.4 g) potassium carbonate (0.2 g) and ethyl bromoacetate (200 μl) in N,N-dimethylformamide (7 ml) was heated at 65° C. for 1 1/4 hours. The reaction mixture was poured into ice water and the solid ester which precipitated was removed by filtration then dissolved in methanol (15 ml) containing water (1 ml) and 10N sodium hydroxide (1 ml). After 1/2 hour the methanol solution was poured into dilute aqueous hydrochloric acid, extracted with ether which was washed with water, brine, dried over MgSO4 and evaporated in vacuo. Trituration of the residue with methylene chloride gave 0.35 g of (1,2-dichloro-8-oxo-5a-propyl-5a,6,7,8-tetrahydrodibenzofuran-3-yl)acetic acid which melted at 248°-250° C.

Quelle