Sodium Hydroxide → 5-Phenyl-2-Thiophenecarboxylic Acid

HRID 896460

Reaktionsgleichung

Reaktionsgleichung von HRID 896460
[C:1]1([C:7]2[S:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14]P([O-])(O)=O.[K+].[O-]Cl=O.[Na+].[OH-].[Na+]>C1COCC1.CC(O)(C)C.O>[C:1]1([C:7]2[S:11][C:10]([C:12]([OH:14])=[O:13])=[CH:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

8

Edukt 4

HCID 14798Sodium HydroxideHCID 1770535-Phenylthiophene-2-carbaldehydeHCID 516951Monobasic potassium phosphateHCID 23668197Sodium Chlorite

Produkt 1

HCID 7364945-Phenyl-2-Thiophenecarboxylic AcidAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel2×HCID 6386tert-ButanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product of Step 3a (750 mg, 4 mmol) is dissolved in a mixture of THF, t-BuOH, and water (2:1:1, 60 mL). KH2PO4 (1.36 g, 10 mmol) is added followed by NaClO2 (900 mg, 10 mmol). The mixture is stirred at rt for 5 days. Aqueous NaOH (2M, 10 mL) is added, and a majority of the organic solvents are removed in vacuo yielding an aqueous suspension. This suspension is diluted with water and washed three times with CH2Cl2. The aqueous layer is acidified to pH<6 with 25% H2SO4 and the product is extracted three times with CH2Cl2. The combined organic washes are dried over Na2SO4, filtered and concentrated in vacuo to yield 5-phenylthiophene-2-carboxylic acid (417 mg, 51%). MS for C11H8O2S (ESI) (M−H)− m/z 203.

Aufarbeitung

  1. customa majority of the organic solvents are removed in vacuo
  2. customyielding an aqueous suspension
  3. washwashed three times with CH2Cl2
  4. extractionthe product is extracted three times with CH2Cl2
  5. dry with materialThe combined organic washes are dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8d9341c200af4a11b7564baeaf984503
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06919359B2

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