Ethanol → 5-Hexyl-2-thiophenecarboxylic acid

HRID 892380Notes

Reaction equation

HRID 892380 reaction equation
[CH2:1]([C:7]1[S:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].C([OH:16])C.[OH-].[Na+]>O.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([C:7]1[S:11][C:10]([C:12]([OH:16])=[O:13])=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 114696515-Hexylthiophene-2-carboxaldehyde

Product 1

HCID 131282695-Hexyl-2-thiophenecarboxylic acidYield 76.6%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent2×

Procedure

In a 500 ml-four-necked flask, 10.0 g (5.10×10-2 mol) of 5-hexylthiophene-2-carbaldehyde, 60 ml of ethanol and a solution of 19.0 g of AgNO3 in 60 ml of water were placed. A solution of 10.2 g of NaOH in 300 ml of water was added dropwise to the mixture in 30 min. at room temperature, followed by stirring for 1.5 hours. After the reaction, the reaction mixture was subjected to filtration, and the filtrate was acidified with 6N-HCl to precipitate a crystal. The crystal was recovered by filtration to provide a crude product. The product was subjected to recrystallization from 50% hydrous ethanol to obtain 8.28 g of a pure product (yield: 76.6%).

Workup

  1. customAfter the reaction
  2. filtrationthe reaction mixture was subjected to filtration
  3. customto precipitate a crystal
  4. filtrationThe crystal was recovered by filtration
  5. customto provide a crude product
  6. customThe product was subjected to recrystallization from 50% hydrous ethanol

Sources & evidence

ORD record
ord-e308e905050840908a174909012b7afa
Source dataset
uspto-grants-1992_06
Patent number
US05118441

Reaction notes

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