Benzenemethanol, 4-(diethoxymethyl)- → 4-(Hydroxymethyl)benzaldehyde

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Alcohol 1 (10.09 g, 48 mmol) was dissolved in a mixture of THF (100 ml) and 2 M HCl (100 ml) and stirred for 1 hour. The solvent was evaporated and the residue obtained was dissolved in ethyl acetate (100 ml) and water (100 ml). The phases were separated and the organic phase was washed with water (100 ml), dried over magnesium sulphate, and evaporated to yield 2 as a white solid (6.54 g, 48 mmol, 100%). Rf=0.54 (ethyl acetate/chloroform, 1:1); νmax=3327, 1689, 1607, 1206, 1010, 823 cm−1; 1H NMR (250 MHz, CDCl3) δ=10.02 (s, 1H, CHO), 7.89 (d, 3J(H,H)=8.1 Hz, 2H, ArCH α to CHO), 7.54 (d, 3J(H,H)=8.1 Hz, 2H, ArCH α to CH2OH), 4.82 (d, 3J(H,H)=5.9 Hz, 2H, CH2OH), 1.94 (t, 3J(H,H)=5.9 Hz, 1H, CH2OH); 13C NMR (75 MHz, CDCl3) δ=192.0 (CHO), 147.7 (ArCCOH), 135.7 (ArCCHO), 130.0 (ArCH α to ArCCHO), 127.0 (ArCH α to ArCCH2OH), 64.6 (CH2OH); HRMS (ESI−): m/z calculated for C8H7O2 [M−H]−: 135.0446, found 135.0448; elemental analysis calcd (%) for C8H8O2 (136.15): C, 70.57; H, 5.92. found: C, 70.70; H, 6.00.

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