Reaction #64718

Reaction equation

water

2-[bis(4-acetoxyphenyl)methyl]benzoyl chloride

m-anisidine

triethylamine

→

desired product

2-[Bis(4-hydroxyphenyl)methyl]-N-(3-methoxyphenyl)benzamide

Solvents

methylene chloride

methylene chloride

Conditions

Workup

1. 1
   Otheras obtained in Reference Example 2
2. 2
   OtherThe organic layer was separated off
3. 3
   Extractionthe water layer was extracted with chloroform
4. 4
   Washthe combined organic layer was washed with 2N aqueous hydrochloric acid solution
5. 5
   Dryingdried over anhydrous magnesium sulfate
6. 6
   ConcentrationThe organic layer was concentrated under reduced pressure
7. 7
   workup.ADDITIONthe residue was suspended in a mixture of 50 ml of saturated aqueous sodium hydrogencarbonate solution and 50 ml of methanol
8. 8
   Temperaturethe resulting suspension was heated
9. 9
   Temperatureunder reflux for 2 hours
10. 10
    ConcentrationThe suspension was concentrated under reduced pressure, and water
11. 11
    workup.ADDITIONwas added to the residue
12. 12
    ExtractionThe resulting mixture was extracted with ethyl acetate
13. 13
    Dryingthe extract was dried over anhydrous magnesium sulfate
14. 14
    ConcentrationThe residue was concentrated under reduced pressure
15. 15
    Otherwas recrystallized

Procedure

In 20 ml of methylene chloride were dissolved 0.62 g of m-anisidine and 5 ml of triethylamine. To this solution was added dropwise under ice cooling 20 ml of methylene chloride containing 2.64 g of 2-[bis(4-acetoxyphenyl)methyl]benzoyl chloride as obtained in Reference Example 2. After stirring for 30 minutes, water was added thereto. The organic layer was separated off, and the water layer was extracted with chloroform. The chloroform layer was combined with the organic layer, and the combined organic layer was washed with 2N aqueous hydrochloric acid solution and dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure, and the residue was suspended in a mixture of 50 ml of saturated aqueous sodium hydrogencarbonate solution and 50 ml of methanol, and the resulting suspension was heated under reflux for 2 hours. The suspension was concentrated under reduced pressure, and water was added to the residue. The resulting mixture was extracted with ethyl acetate, and the extract was dried over anhydrous magnesium sulfate. The residue was concentrated under reduced pressure, and was recrystallized to afford 1.54 g of the desired product.

Source