Sodium Hydroxide → 5-Phenyl-2-Thiophenecarboxylic Acid

HRID 2301853Notes

Reaction equation

HRID 2301853 reaction equation
[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

Participants

8

Reactant 4

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

Product 1

HCID 7364945-Phenyl-2-Thiophenecarboxylic AcidYield 51%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The product of Step 1a (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 room temperature 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 the desired product (417 mg, 51%). MS for C11H8O2S (ESI) (M−H)− m/z 203.

Workup

  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

Sources & evidence

ORD record
ord-480277a9004c4224bc41266d419b44c2
Source dataset
uspto-grants-2002_12
Patent number
US06500840B2

Reaction notes

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