Benzaldehyde, 3-(benzoyloxy)- synthesis
- Product Name:Benzaldehyde, 3-(benzoyloxy)-
- CAS Number:33696-06-9
- Molecular formula:C14H10O3
- Molecular Weight:226.23
Yield:33696-06-9 99%
Reaction Conditions:
with dmap;N-ethyl-N,N-diisopropylamine in dichloromethane at 20;
Steps:
2.1. 3-formylphenyl benzoate (1)
3-hydroxy benzaldehyde (4.88 g, 40 mmol) and N,N-diisopropylethylamine ( 7.8 g, 10.4 mL, 60 mmol, 1.5 eq. ) was dissolved in dimethyl chloride (100 mL) forming a yellow solution in ice-water bath. Following the addition of a catalytic amount of DMAP, benzoyl chloride (8.4 g, 6.9 mL, 60 mol, 1.5 eq.) was added dropwise. Afterwards, the mixture was stirred at room temperature overnight. Finally, an orange solution was obtained. The reaction was monitored with TLC. The organic phase was washed with saturated NaHCO3 aq. (60 mL), water (60 mL) and brine (60 mL) successively. After dried with anhydrous sodium sulfate, the organic phase was concentrated. The product 1 was separated with silica gel (300-400 mesh) column chromatography, using petroleum ether and ethyl acetate (V/V, 10:1) as eluent to afford a colorless oil (9.02 g, yield 99 %). 1H NMR (400 MHz, CDCl3) δ 10.07 (s, 1H), 8.27- 8.21 (m, 2H), 7.84 (dt, J = 7.6, 1.3 Hz, 1H), 7.79 (dd, J = 2.4, 1.5 Hz, 1H), 7.72 - 7.67 (m, 1H), 7.65 (t, J = 7.8 Hz, 1H), 7.59 - 7.51 (m, 3H). 13C NMR (101 MHz, CDCl3) δ 191.18, 164.90, 151.55, 137.84, 133.96, 130.26, 130.23, 128.99, 128.71, 127.95, 127.34, 122.55.
References:
Gao, Yuqi;Lin, Yuxing;Liu, Tingting;Zhang, Xiaomeng;Xu, Feng;Liu, Pan;Du, Lupei;Li, Minyong [Chinese Chemical Letters,2019,p. 63 - 66] Location in patent:supporting information
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