4-Hydroxybenzaldehyde → p-Dodecyloxybenzaldehyde

Participants

Reaction Conditions

Reaction Steps

4-Hydroxybenzaldehyde (8.00 g, 6.55×10−2 mol), 1-bromododecane (16.50 ml, 6.87×10−2 mol), K2CO3 (9.05 g, 6.55×10−2 mol) and dry DMF (100 ml) were added to a two-neck round-bottom flask. The reaction mixture was stirred at 105° C. for 21.5 h under Ar. After cooling, the solution was diluted with H2O, 2M HCl and extracted three times with CH2Cl2. The combined organic layers were washed with aqueous NaHCO3, H2O and dried over Na2SO4. The product was chromatographed on silica gel with 1:1 hexane:CH2Cl2 as the eluent. Yield=19.02 g (100% based on 8.00 g of 4-hydroxybenzaldehyde). 1H NMR (250 MHz, CDCl3): δ 9.88 (s, 1H, —CHO), 7.83 (d, 2H, J=8.8 Hz, Ph), 6.99 (d, 2H, J=8.7 Hz, Ph), 4.04 (t, 2H, J=6.5 Hz, OCH2), 1.82 (quint, 2H, J=6.9 Hz, OCH2CH2), 1.40-1.54 (m, 2H, —CH2—), 1.16-1.40 (m, 16H, —CH2—), 0.88 (t, 3H, J=6.5 Hz, —CH3). CI MS m/z: 291.232 ((M+H)+) (calcd 291.232).

Provenance & Evidence