Reaction #731268

Reaction equation

HCl

Water

3-(4-Methanesulfonyl-phenoxy)-5-(2-methoxy-1-methyl-ethoxy)benzonitrile

sodium hydroxide

→

title product

Yield 100.0%

3-(4-Methanesulfonyl-phenoxy)-5-(2-methoxy-1-methyl-ethoxy)benzoic acid

Yield 100.0%

Solvents

MTBE

ethanol

Conditions

Workup

1. 1
   workup.ADDITIONcharged to a 5 ml round bottomed flask
2. 2
   Otherequipped with a condenser
3. 3
   TemperatureThe reaction mixture was heated
4. 4
   Temperatureto reflux for 18 hours
5. 5
   Otherthe solvent was evaporated in vacuo
6. 6
   Otherthe residue was partitioned between water (10 ml) and MTBE (10 ml)
7. 7
   Otherthe layers were separated
8. 8
   workup.ADDITIONwas added
9. 9
   Extractionto extract the product
10. 10
    ExtractionThis MTBE extract
11. 11
    Dryingwas dried over MgSO4
12. 12
    Otherevaporated in vacuo

Procedure

3-(4-Methanesulfonyl-phenoxy)-5-(2-methoxy-1-methyl-ethoxy)benzonitrile (0.1 g, 0.27 mmol) was dissolved in ethanol (1.0 ml) and charged to a 5 ml round bottomed flask equipped with a condenser. Water (0.2 ml, 11.1 mmol) was added, followed by sodium hydroxide (18.9M in water, 0.2 ml, 3.78 mmol). The reaction mixture was heated to reflux for 18 hours. The reaction mixture was cooled to room temperature, the solvent was evaporated in vacuo, the residue was partitioned between water (10 ml) and MTBE (10 ml) and the layers were separated. The aqueous phase was acidified to pH 1 with 2M HCl (2.5 ml, 5 mmol) and MTBE (10 ml) was added to extract the product. This MTBE extract was dried over MgSO4, and then evaporated in vacuo to give the title product as a white solid (0.1 g, 100% yield).

Source