[OH:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5].Br[CH2:12][CH:13]([O:16][CH3:17])[O:14][CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:15][O:14][CH:13]([O:16][CH3:17])[CH2:12][O:1][C:2]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][C:3]=1[CH:4]=[O:5]To a solution of 100 mg (0.73 mmol) of 2-hydroxy-5-methyl-benzaldehyde in DMF (1 ml) were added 109 μl (0.92 mmol) of 2-bromo-1,1-dimethoxy-ethane and 112 mg (0.81 mmol) of potassium carbonate. The reaction mixture was heated to reflux for 90 min. Then water was added at RT and the mixture was extracted with ether. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated to yield 2-(2,2-dimethoxy-ethoxy)-5-methyl-benzaldehyde as a yellow oil (154 mg, 93%). 1HNMR (CDCl3, 300 MHz): δ 2.32 (s, 3H), 3.48 (s, 6H), 4.09 (d, J=5.3 Hz, 2H), 4.75 (t, J=5.3 Hz, 1H), 6.89 (d, J=8.4 Hz, 1H), 7.34 (dd, J=8.4 and 2.3 Hz, 1H), 7.64 (d, J=2.3 Hz, 1H), 10.48 (s, 1H).
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