Toluene → 4-Chlorobenzenepropanol

Temperature

5 °C

95.38 g (400 mmol) of p-chloroiodobenzene, 34.85 g (600 mmol) of ally alcohol, 0.089 g (0.4 mmol) of palladium acetate and 47.99 g (2,000 mmol) of sodium hydrogencarbonate, were added to 200 ml of dimethylformamide (DMF), followed by heating until the internal temperature of the suspension became 50° C. The heating was continued for 7 hours, and after confirming the formation of the aldehyde compound by gas chromatogram, the suspension was cooled to 5° C. Then, 4.54 g (120 mmol) of sodium borohydride was added, followed by stirring for 30 minutes. Then, 100 ml of a saturated ammonium chloride aqueous solution, 100 ml of water and 200 ml of toluene were added, followed by stirring for one hour. After removing insolubles by Celite filtration, liquid separation was carried out, and the water layer was extracted again with 200 ml of toluene. The tolune layers were put together, concentrated and then distilled (107° C./1 mmHg) to obtain 63.4 g (y 93%) of 3-(p-chlorophenyl)-1-propanol {compound (1)} as a colorless oily substance. From the analysis by gas chromatography, this product was found to contain 6% of the branched isomer.

1. temperatureby heating until the internal temperature of the suspension
2. custombecame 50° C
3. stirringby stirring for one hour
4. customAfter removing insolubles
5. filtrationby Celite filtration, liquid separation
6. extractionthe water layer was extracted again with 200 ml of toluene
7. concentrationconcentrated
8. distillationdistilled (107° C./1 mmHg)

ORD record

ord-a073c4e2c8494b34b168d7535290d270

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06407298B1