反应详情

温度

60 °C

To a stirred suspension of 4-hydroxybenzaldehyde (425.8 g) and K2CO3 (807.6 g) in acetone (2,960 ml) at reflux temper-ature of about 60° C. under a nitrogen atmosphere, was added dropwise 3-bromo-propyne (502.4 g) over a period of 2 hours. The reaction was heated at reflux for 3 more hours. After cooling to room temperature the reaction mixture was filtered and the excess of K2CO3 removed and washed several times with acetone. The filtrate was washed with saturated aqueous solution of NaHCO2 and NaCl. The aqueous phase was extracted with diethyl ether. The combined organic extracts were dried over Na2SO4, filtered and concentrated to a volume of 1 liter. The solution was kept in the refrigerator overnight. The crystals were filtered out and washed with cold diethyl ether. The filtrate was kept in the refrigerator and some more crystals were formed and removed. This procedure was repeated 3 times resulting in 1,385.26 g of 4-(2-propynyloxy) benzaldehyde in 83% yield. The material was analysed by gas chromatography, and shown to be 99.9% pure. Infrared and mass spectroscopic analysis confirmed the structure.

1. temperatureThe reaction was heated
2. temperatureat reflux for 3 more hours
3. temperatureAfter cooling to room temperature the reaction mixture
4. filtrationwas filtered
5. customthe excess of K2CO3 removed
6. washwashed several times with acetone
7. washThe filtrate was washed with saturated aqueous solution of NaHCO2 and NaCl
8. extractionThe aqueous phase was extracted with diethyl ether
9. dry with materialThe combined organic extracts were dried over Na2SO4
10. filtrationfiltered
11. concentrationconcentrated to a volume of 1 liter
12. customwas kept in the refrigerator overnight
13. filtrationThe crystals were filtered out
14. washwashed with cold diethyl ether
15. customsome more crystals were formed
16. customremoved