Ethanol → 5-Hexyl-2-thiophenecarboxylic acid

HRID 1608450Notes

Reaction equation

HRID 1608450 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 5 liter-four-necked flask, 90.0 g (4.59×10-1 mol) of 5-hexylthiophene-2-carbaldehyde, 540 ml of ethanol and a solution of 171.0 g of AgNO3 in 540 ml of water were placed. A solution of 91.8 g of NaOH in 270 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 74.5 g of a pure product (yield: 76.6%).

Workup

  1. customAfter the reaction
  2. filtrationthe reaction mixture was subjected to filtration
  3. customHCl to 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-807beb1c76b34a82bf39aae9d0c2d54b
Source dataset
uspto-grants-1995_03
Patent number
US05395551

Reaction notes

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