반응 #675091

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3-methyl-2,4-bis(tetrahydro-2H-pyran-2-yloxy)benzaldehyde

2,4-Dihydroxy-3-methylbenzaldehyde

3,4-dihydro-2H-pyran

pyridinium para-toluenesulfonate

→

title compound

2-hydroxy-3-methyl-4-(tetrahydro-2H-pyran-2-yloxy)benzaldehyde

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후처리

1. 1
   기타to get 15.0 g of crude title product
2. 2
   기타Crude product was purified by column chromatography

실험 절차

By following Example 2 procedure, 10.0 g of 2,4-Dihydroxy-3-methylbenzaldehyde was reacted with 48.3 g of 3,4-dihydro-2H-pyran in the presence of 1.6 g of pyridinium para-toluenesulfonate to get 15.0 g of crude title product. Formation of 3-methyl-2,4-bis(tetrahydro-2H-pyran-2-yloxy)benzaldehyde was not noticed either by GC or TLC of the crude sample. Crude product was purified by column chromatography to get the title compound as white solid. DSC: 58.2° C. (peak). IR (KBr): 3125, 2946, 2870, 2747, 1645, 1623, 1585, 1494, 1431, 1388, 1356, 1327, 1288, 1246, 1204, 1181, 1121, 1091, 1036, 1022, 955, 921, 895, 872, 799, 758, 712, and 642 cm−1. 1H-NMR (CDCl3, 400 MHz): δ 11.49 (s, 1H, exch. with D2O, OH), 9.72 (s, 1H, CHO), 7.33 (d, J=8.8 Hz, 1H, H-6), 6.78 (d, J=8.8 Hz, 1H, H-5), 5.58 (t, J=2.8 Hz, 1H, OCHO), 3.81 (dt, J=2.8 Hz, 11.2 Hz, 1H, CH2O), 3.61-3.66 (m, 1H, CH2O), 2.15 (s, 3H, ArCH3), 2.00-2.05 (m, 1H, CH2CHO), 1.89-1.93 (m, 2H, CH2CHO and CH2CH2CHO), 1.62-1.75 (m, 3H, OCH2CH2CH2). 13C NMR (CDCl3, 100 MHz): δ 194.80 (CHO), 161.62 (C-4), 161.20 (C-2), 132.71 (C-6), 115.47 (C-1), 114.05 (C-3), 106.17 (C-5), 95.67 (OCHO), 61.89 (C-6′), 30.00 (C-2′), 24.97 (C-5′), 18.36 (C-4′), 7.38 (ArCH3). Mass (EI-MS): 236.24 (M), 235.10 (M−1).

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