Propanal → HCID 86757532, compound

Temperature

20 °C

Into a 2 L Morton flask equipped with a mechanical air stirrer, temperature probe, Nitrogen inlet, autojack, and cooling bath was placed methanol (350 mL) and NaOH (31.25 g, 0.78 mol) dissolved in water (93.75 mL). 2-Methyl-3-phenyl-propanal (100 g, 0.68 mol) was added to the resulting mixture with stirring at 20° C. Over a period of 5 hours at an exponentially decreasing rate, propionaldehyde (48.82 mL, 39.25 g, 0.68 mol) was added to the mixture via a syringe pump while maintaining the reaction temperature at 14-20° C. The following propionaldehyde addition rate profile was used: 0.179 mL/min for two hours; 0.162 mL/min for one hour; and 0.147 mL/min for two hours. The reaction mixture was stirred for an additional 20 min at 14-20 ° C. Acetic acid (47 mL) was then added to the reaction mass followed by 100 mL of a saturated aqueous solution of sodium chloride. The mixture was extracted with two 100 mL portions of MTBE. The organic layers were combined and washed with two 100 mL portions of a saturated aqueous solution of sodium bicarbonate solution then with a saturated aqueous solution of.sodium chloride, dried (MgSO4), filtered, and roto-evaporated to give 2, 4-dimethyl-5-phenylpent-2-enal as a yellow liquid isomeric mixture (118.9 g).

1. customInto a 2 L Morton flask equipped with a mechanical air stirrer
2. temperaturetemperature probe, Nitrogen inlet, autojack, and cooling bath
3. temperaturewhile maintaining the reaction temperature at 14-20° C
4. wait0.179 mL/min for two hours
5. wait0.162 mL/min for one hour
6. waitand 0.147 mL/min for two hours
7. stirringThe reaction mixture was stirred for an additional 20 min at 14-20 ° C
8. extractionThe mixture was extracted with two 100 mL portions of MTBE
9. washwashed with two 100 mL portions of a saturated aqueous solution of sodium bicarbonate solution
10. dry with materialsodium chloride, dried (MgSO4)
11. filtrationfiltered
12. customroto-evaporated

ORD record

ord-622d4acaefbc40f1a870fadeaa86176a

Source dataset

uspto-grants-2001_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06310033B1