Hydrochloric Acid → (+/-)-5-(2-Formyl-3-hydroxyphenoxy)-2-methylpentanoic acid
Reaktionsgleichung
[CH:1]([C:3]1[C:19]([O:20]C)=[CH:18][CH:17]=[CH:16][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11])=[O:2].[I-].[Mg+2].[I-].C(C1C(O)=CC=CC=1OCCCC(C)C(OCC)=O)=O.Cl>O1CCCC1.CCOCC>[CH:1]([C:3]1[C:19]([OH:20])=[CH:18][CH:17]=[CH:16][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][CH:9]([CH3:15])[C:10]([OH:12])=[O:11])=[O:2]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
To a stirred solution of (±)-ethyl 5-(2-formyl-3-methoxyphenoxy)-2-methylpentanoate (5.3 g, 0.018 M) in dry tetrahydrofuran (50 ml) was added dropwise a solution of magnesium iodide (7.44 g, 0.027 M) in dry ether (100 ml). The mixture was then stirred under reflux (51/2 hr). The cooled mixture, containing (±)-ethyl 5-(2-formyl-3-hydroxyphenoxy)-2-methylpentanoate, was poured into 10% hydrochloric acid (50 ml), the organic layer was separated and the aqueous phase extracted with ethyl acetate. The combined organic solutions were washed with water and extracted with 2 N sodium hydroxide solution. The combined extracts were acidified with concentrated hydrochloric acid with cooling and the solid produced filtered off and washed with water to give (±)-5-(2-formyl-3-hydroxyphenoxy)-2-methylpentanoic acid, m.p. 70°-70.5° C. from benzene/petrol.
Aufarbeitung
- temperatureunder reflux (51/2 hr)
- customthe organic layer was separated
- extractionthe aqueous phase extracted with ethyl acetate
- washThe combined organic solutions were washed with water
- extractionextracted with 2 N sodium hydroxide solution
- temperaturewith cooling
- customthe solid produced
- filtrationfiltered off
- washwashed with water
Quellen und Nachweise
- ORD-Eintrag
- ord-e476b8d4c8324259967cc8631cb24524
- Quelldatensatz
- uspto-grants-1983_10
- Patentnummer
- US04410537
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