Sodium Hydroxide → 5-Phenoxythiophene-2-carboxylic acid

5-Phenoxy-thiophene-2-carboxaldehyde (325 mg, 1.6 mmol) is dissolved in a mixture of THF (10 mL), t-BuOH (5 mL) and water (5 mL). NaH2PO4 (650 mg, 4.8 mmol) is added followed by NaClO2 (432 mg, 4.8 mmol). The resulting mixture is stirred for 24 hours at room temperature. Aqueous NaOH (2M, 5 mL) is added, and the organic solvents are removed in vacuo. The resulting aqueous suspension is poured into water (10 mL) and washed with ether (3×50 mL). The aqueous layer is acidified to pH<2 with 25% H2SO4 then washed with CH2Cl2 (3×50 mL). The combined organic washes are dried over Na2SO4, filtered and concentrated in vacuo. The crude product is dissolved in hot aqueous acetone and filtered. The solvents are gradually removed until a precipitate forms. The solid is collected by filtration and dried in vacuo to yield the desired product (192 mg, 55%). MS for C11H7O3S (ESI) (M−H)+ m/z 219.

1. customthe organic solvents are removed in vacuo
2. additionThe resulting aqueous suspension is poured into water (10 mL)
3. washwashed with ether (3×50 mL)
4. washthen washed with CH2Cl2 (3×50 mL)
5. dry with materialThe combined organic washes are dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. dissolutionThe crude product is dissolved in hot aqueous acetone
9. filtrationfiltered
10. customThe solvents are gradually removed until a precipitate forms
11. filtrationThe solid is collected by filtration
12. customdried in vacuo

ORD record

ord-07d87fb8d44d4e1c93b590bc059a4314

Source dataset

uspto-grants-2003_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06599916B2