Potassium Hydroxide → a-Methoxymethyl-3,5-dimethoxy-4-(beta-methoxyethoxy)methoxycinnamic acid

A solution of 2.6 g (22.0 mmol) of methyl 3-methoxy-propionate in 5 ml of tetrahydrofuran was added to a solution of 666 mg of sodium hydride in 15 ml of tetrahydrofuran solution with ice cooling, subsequently to the resulting solution was added a solution of 3 g (1.1 mmol) of 3,5-dimethoxy-4-(β-methoxyethoxy)methoxybenzaldehyde in 10 ml of tetrahydrofuran. The mixture was stirred at room temperature for 17 hours. The mixture was extracted with 60 ml of ethyl acetate after adding ice to the solution. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The oily product thus obtained was dissolved in 20 ml of tetrahydrofuran. An aqueous potassium hydroxide solution (740 mg/5 ml) was added to the solution. The mixture was stirred at room temperature for 21 hours. The solution was evaporated under reduced pressure. A 40 ml of water was added to the residue, and the aqueous solution was washed with 30 ml of ethyl acetate. The aqueous layer was neutralized with acetic acid and extracted with 60 ml of methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give 2.5 g (yield 63.2%) of a desired α-methoxymethyl-3,5-dimethoxy-4-(β-methoxyethoxy)-methoxycinnamic acid.

1. extractionThe mixture was extracted with 60 ml of ethyl acetate
2. additionafter adding ice to the solution
3. washThe organic layer was washed with water
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe oily product thus obtained
7. stirringThe mixture was stirred at room temperature for 21 hours
8. customThe solution was evaporated under reduced pressure
9. additionA 40 ml of water was added to the residue
10. washthe aqueous solution was washed with 30 ml of ethyl acetate
11. extractionextracted with 60 ml of methylene chloride
12. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
13. customevaporated under reduced pressure

ORD record

ord-018d6f26613a453e8400285b80a109e8

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05478856