[CH:1]1(Cl)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O:7]=[CH:8][C:9]1[CH:17]=[CH:16][C:13]([O:14][CH3:15])=[C:11]([OH:12])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:1]1([O:12][C:11]2[CH:10]=[C:9]([CH:17]=[CH:16][C:13]=2[O:14][CH3:15])[CH:8]=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1A mixture of cyclopentyl chloride (8.48 g, 0.08 moles), isovanillin (6.12 g, 0.04 moles) and potassium carbonate (1.1 g, 0.08 moles) in dimethylformamide (4.04 g) was stirred in the reactor (100 mL) at 120 to 125° C. for 1.5 hours. A sample was taken to verify the batch conversion. Result (GC): 0.5 area % isovanillin (target:≦1.0 area %). The mixture was cooled to 20° C. and filtered to remove the solid (potassium bicarbonate, potassium chloride). The wet cake was washed with methanol.
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