[OH-].[K+].[OH:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([NH:10][CH:11]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:13][CH3:14])=[O:9])=[CH:6][C:5]=1[CH3:20].Cl[CH:22]([OH:24])[CH3:23].[CH2:25](O)C>>[CH3:17][CH2:16][CH2:15][CH:11]([NH:10][C:8](=[O:9])[C:7]1[CH:18]=[CH:19][C:4]([O:3][CH2:23][CH2:22][O:24][CH3:25])=[C:5]([CH3:20])[CH:6]=1)[CH2:12][CH2:13][CH3:14]Potassium hydroxide (4 mmol) was dissolved in ethanol (5 mL) and heated at 80° C. 4-hydroxy-3-methyl-N-(1-propyl-butyl)-benzamide (example 58) (1 mmol) was added into the solution followed by chloroethanol (3 mmol). The reaction was stirred overnight at 80° C. The reaction mixture was concentrated down and dissolved in 5% citric acid. The mixture was stirred for 1 hour. The aqueous mixture was extracted three times with ethyl acetate. The combined ethyl acetate was washed with water and dried down over sodium sulfate. The organic layer was concentrated down and purified by HPLC to yield 39% of N-(heptan-4-yl)-4-(2-methoxyethoxy)-3-methylbenzamide. MS (M+H, 308.25).
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