Sodium Hydroxide → 5-Phenyl-2-Thiophenecarboxylic Acid

HRID 1359626

反応式

HRID 1359626 の反応式
[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

参加物

8

反応物 4

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

生成物 1

HCID 7364945-Phenyl-2-Thiophenecarboxylic Acid収率 51%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6386tert-Butanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5479d77b58524cbc9c803c907ba77bc6
出典データセット
uspto-grants-2003_07
特許番号
US06599916B2

関連ノート

読み込み中…