[OH-].[Na+].[CH3:3]I.[OH:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH:17]([CH2:19][CH3:20])[CH3:18])[O:12][C:11]([CH3:22])([CH3:21])[CH2:10][C:9]2=[O:23]>ClCCl.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C>[CH3:3][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[O:16][CH:17]([CH2:19][CH3:20])[CH3:18])[O:12][C:11]([CH3:21])([CH3:22])[CH2:10][C:9]2=[O:23]In 40 ml of a 5% sodium hydroxide solution 5.2 g (20 millimoles) of 6-hydroxy-7-sec. butoxy-2,2-dimethyl-4-chromanone are dissolved whereupon 80 ml of dichloro methane and 0.5 g of triethyl benzyl ammonium chloride are added and the mixture is intensively stirred at room temperature for 30 minutes. After the addition of 4.25 g (1.9 ml, 30 millimoles) of methyl iodide the reaction mixture is stirred for further 2 hours. The organic phase is separated, washed twice with 50 ml of water each, dried over sodium sulfate and the solvent is removed. The residue is crystallized from 90% ethanol. Thus 5.34 g of the desired compound are obtained, yield 96%. Mp.: 92.5°-93° C.
Loading…