Diethyl Ether → 4-[(4-Phenoxy)-phenoxy]-butyric acid diethylamide
Reaction equation
[K].C([O-])(C)(C)C.[O:7]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:21]([N:23]([CH2:30][CH3:31])[C:24](=[O:29])[CH:25](Cl)[CH2:26][CH3:27])[CH3:22].C(OCC)C>CS(C)=O>[CH2:21]([N:23]([CH2:30][CH3:31])[C:24](=[O:29])[CH2:25][CH2:26][CH2:27][O:20][C:17]1[CH:16]=[CH:15][C:14]([O:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:19][CH:18]=1)[CH3:22]Participants
Procedure
17 g of potassium-tert.-butanolate is added at 10° C to a solution of 28 g of 4-phenoxy-phenol in 100 ml of anhydrous dimethylsulphoxide. After the base has completely dissolved, an addition is made dropwise in the course of 2 hours, with stirring, of 26.5 g of chlorobutyric acid diethylamide dissolved in 20 ml of dimethylsulphoxide and the whole is further stirred overnight at room temperature. For further processing, the reaction mixture is poured into ice water, and extraction is repeatedly performed with diethyl ether. The combined ether phases are washed four times with cold 10% potassium hydroxide solution and subsequently repeatedly with water; they are then dried by means of sodium sulphate. After the ether has been distilled off, there is obtained crude 4-[(4-phenoxy)-phenoxy]-butyric acid diethylamide, which is purified by chromatography on silica gel (eluant: ether/hexane 1:3), and recrystallised from isopropanol/hexane, M.P. 73°-74° C.
Workup
- dissolutionAfter the base has completely dissolved
- additionan addition
- customis made dropwise in the course of 2 hours
- washThe combined ether phases are washed four times with cold 10% potassium hydroxide solution
- dry with materialthey are then dried by means of sodium sulphate
- distillationAfter the ether has been distilled off
Sources & evidence
- ORD record
- ord-76fb279065bc40a7a878f2a70618ff83
- Source dataset
- uspto-grants-1977_12
- Patent number
- US04064269
Reaction notes
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