1-Bromopentane → 3-Methoxy-2-(pentyloxy)benzaldehyde

Temperature

100 °C

2-Hydroxy-3-methoxybenzaldehyde (3.00 g, 19.7 mmol) and DMF (25 ml) were mixed, and potassium carbonate (3.00 g, 22.0 mmol) and bromopentane (2.73 ml, 22.0 mmol) were successively added to this solution. The reaction mixture was stirred at 100° C. for 2 hours and the obtained solid was filtered. Water (20 ml) and ethyl acetate (50 ml) were added for separation. The aqueous layer was extracted twice with ethyl acetate (25 ml). The organic layers were combined, washed twice with saturated brine (20 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure to give a crude product of 3-methoxy-2-pentyloxybenzaldehyde. (2) THF (30 ml) and methyl (triphenylphosphoranilidene)acetate (7.36 g, 22.0 mmol) were added to the above-mentioned compound. The mixture was re iuxed under heating for 5.5 hours and THF was evaporated under reduced pressure. Hexane (100 ml) was added to the obtained residue, and the precipitated crystals were filtered off. The filtrate was concentrated under reduced pressure. To the obtained residue were added ethanol (40 ml) and a 1N aqueous sodium hydroxide solution (40 ml). The mixture was refluxed under heating for 1 hour. After removing ethanol by evaporation under reduced pressure, concentrated hydrochloric acid was added to make the aqueous layer acidic. The aqueous layer was extracted twice with ethyl acetate (70 ml). The organic layers were combined, washed 3 times with saturated brine (40 ml) and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and the filtrate was concentrated under reduced pressure. The obtained crude crystals were recrystallized from ethyl acetate to give 3- (3-methoxy-2-pentyloxyphenyl)cinnamic acid (3.82 g, 73% in 3 steps) as colorless needles.

1. filtrationthe obtained solid was filtered
2. additionWater (20 ml) and ethyl acetate (50 ml) were added for separation
3. extractionThe aqueous layer was extracted twice with ethyl acetate (25 ml)
4. washwashed twice with saturated brine (20 ml)
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationThe drying agent was filtered off
7. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-33aabcef84064bb58d2ce062fb600623

Source dataset

uspto-grants-2000_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06017919