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

Participants

Reaction Conditions

Reaction Steps

4-(Diethoxymethyl)benzaldehyde (10 g, 48 mmol) was dissolved in methanol (200 ml) and cooled to 0° C. NaBH4 (4.54 g, 120 mmol, 2.5 eq) was then added slowly and the reaction mixture was stirred for 1 hour, after which the solvent was evaporated. 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 1 as a clear oil (10.09 g, 48 mmol, 100%). 1H NMR (300 MHz, CDCl3) δ=7.48 (d, 3J(H,H)=8.1 Hz, 2H, ArCH α to CH2OH), 7.37 (d, 3J(H,H)=8.1 Hz, 2H, ArCH α to CH(OEt)2), 5.51 (s, 1H, CH(OEt)2), 4.70 (d, 3J(H,H)=5.9 Hz, 2H, CH2OH), 3.61 (dq, 3J(H,H)=7.1 Hz, 2J(H,H)=9.5 Hz, 2H, CH2CH3), 3.56 (dq, 3J(H,H)=7.1 Hz, 2J(H,H)=9.5 Hz, 2H, CH2CH3), 1.75 (t, 3J(H,H)=5.9 Hz, 1H, CH2OH), 1.24 (t, 3J(H,H)=7.1 Hz, 6H, CH2CH3); 13C NMR (75 MHz, CDCl3) δ=140.9 (ArCCH2OH), 138.6 (ArCCH(OEt)2), 126.9 (ArCH α to ArCCH2OH), 126.8 (ArCH α to ArCCH(OEt)2), 101.3 (CH(OEt)2), 65.1 (CH2OH), 61.0 (OCH2CH3), 15.2 (OCH2CH3).

Provenance & Evidence