Diethyl Ether → HCID 23510444, compound

Under nitrogen atmosphere, a solution of methoxymethyl-triphenylphosphonium oxide (10.8 g) in Et2O (60 mL) was cooled to 0° C., and thereto was added dropwise a 1.7N solution of t-BuLi in pentane (18.6 mL). After the addition, the mixture was stirred at room temperature for 30 minutes, and cooled to 0° C. To the mixture was added a solution of methyl terephthalaldehyde (5.20 g) in Et2O (80 mL), and the mixture was stirred at 0° C. for 30 minutes, and stirred at room temperature for 80 minuts. To the mixture was added an aqueous NH4Cl solution, and the mixture was extracted twice with Et2O. The organic layer was washed twice with an aqueous NaHSO3 solution, and dried over MgSO4. The solvent was evaporated under reduced pressure to give crude methyl 4-[(E)-2-methoxyethenyl]benzoate (3.71 g). This product was dissolved in a mixture of THF (60 mL)-MeOH (20 mL)-water (20 mL), and thereto was added LiOH hydrate (2.04 g). The mixture was stirred at room temperature for 24 hours, and the solvent was evaporated under reduced pressure. Water was added to the resultant, and the aqueous mixture was washed with ethyl acetate, and cooled to 0° C. The pH value of the mixture was adjusted to pH=3 with a 5% aqueous KHSO4 solution, and the mixture was extracted twice with ethyl acetate, and dried over MgSO4. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column (CHCl3/MeOH=50/1) to give 4-[(E)-2-methoxyethenyl]benzoic acid (1.37 g, 20%).

1. additionAfter the addition
2. temperaturecooled to 0° C
3. stirringthe mixture was stirred at 0° C. for 30 minutes
4. stirringstirred at room temperature for 80 minuts
5. extractionthe mixture was extracted twice with Et2O
6. washThe organic layer was washed twice with an aqueous NaHSO3 solution
7. dry with materialdried over MgSO4
8. customThe solvent was evaporated under reduced pressure
9. customto give crude methyl 4-[(E)-2-methoxyethenyl]benzoate (3.71 g)
10. stirringThe mixture was stirred at room temperature for 24 hours
11. customthe solvent was evaporated under reduced pressure
12. additionWater was added to the resultant
13. washthe aqueous mixture was washed with ethyl acetate
14. temperaturecooled to 0° C
15. extractionthe mixture was extracted twice with ethyl acetate
16. dry with materialdried over MgSO4
17. customThe solvent was evaporated under reduced pressure
18. customthe residue was purified by silica gel column (CHCl3/MeOH=50/1)

ORD record

ord-92945288ee0d452288fb21a0f2700a2f

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06759429B2