[OH-].[K+].[OH:3][C:4]1[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:5]=1[CH:6]=[O:7].[CH3:13][C:14]([CH3:18])=[CH:15][CH2:16]Br>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(OCC)(=O)C>[CH3:13][C:14]([CH3:18])=[CH:15][CH2:16][O:12][C:10]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[C:4]([OH:3])[CH:11]=1
A solution of 6 g (0.11 mol) of potassium hydroxide, 22.7 g (0.1 mol) of benzyltriethylammonium chloride, and 14 g (0.1 mol) of 2,4-dihydroxybenzaldehyde was concentrated in vacuo. The residue was suspended in 100 ml of ethyl acetate and 11.7 ml (0.1 mol) of dimethylallyl bromide was slowlv added to the solution. The mixture was extracted with 100 ml of water, and the organic phase was dried and concentrated in vacuo to give 3.568 g of a residue, from which 4.738 g (20%) of 4-(3-methyl)-but-2-enyloxy-2-hydroxybenzaldehyde identical to that previously described by S. Khan, and M. Krishnamurti in Indian J. Chem. 22B (1983), 276 was purified by column chromatography over silica gel 60 (Merck 0.063-0.200 mm, 200 g) using petroleum ether-ethyl acetate (9:1) as an eluent.
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