Water → HCID 117640723, compound

Temperature

62.5 °C

In a reactor equipped with a stirrer, a cooling condenser, a dropping funnel and a thermometer were placed 7-chloro-1,1-diethoxy-2-heptyne (218.7 g:1.0 mol), para-toluenesulfonic acid (8.0 g:0.05 mol), water (170.0 g) and tetrahydrofuran (42.0 g), and stirred at a reaction mixture temperature of from 60 to 65° C. During stirring, the pressure in the reactor was reduced gradually to 26.7 KPa to distill off refluxing ethanol. After stirring for 5 hours, completion of the reaction was confirmed by gas chromatography. The organic phase separated from the aqueous phase of the reaction mixture was washed with a solution of sodium chloride (5.0 g) in water (150.0 g). The organic phase was subjected to removal of the solvent under reduced pressure, and then the residue was distilled under reduced pressure to obtain 7-chloro-2-heptynal [bp: 66-72° C./0.13 KPa, 137.8 g, 0.95 mol]. [Yield: 95.3%]

1. customIn a reactor equipped with a stirrer, a cooling condenser, a dropping funnel
2. stirringDuring stirring
3. distillationto distill off
4. temperaturerefluxing ethanol
5. stirringAfter stirring for 5 hours
6. customThe organic phase separated from the aqueous phase of the reaction mixture
7. washwas washed with a solution of sodium chloride (5.0 g) in water (150.0 g)
8. customThe organic phase was subjected to removal of the solvent under reduced pressure
9. distillationthe residue was distilled under reduced pressure

ORD record

ord-e4f971514c23462c8821cf19fc1a92f4

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255056B2