Hydrochloric Acid → 5-Dodecylthiophene-2-carboxylic acid

HRID 1196803Notes

Reaction equation

HRID 1196803 reaction equation
[CH2:1]([C:13]1[S:17][C:16]([CH:18]=[O:19])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[OH-].[Na+].[O-:22][Mn](=O)(=O)=O.[K+].Cl>O>[CH2:1]([C:13]1[S:17][C:16]([C:18]([OH:22])=[O:19])=[CH:15][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516875Potassium PermanganateHCID 149850895-Dodecylthiophene-2-carbaldehyde

Product 1

HCID 149850905-Dodecylthiophene-2-carboxylic acidYield 38.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 2 liter-four-necked flask, 30.0 g(1.07×10-1 mol) of 5-dodecylthiophene-2-carbaldehyde, 6.0 g of NaOH, 21.3 g of KMnO4 and 900 ml of water were placed and stirred for 17 hours at room temperature. After the reaction, the reaction mixture was acidified with conc. hydrochloric acid, followed by four times of extraction with 300 ml of ethyl acetate, three times of washing with 500 ml of water, drying with anhydrous magnesium sulfate and distilling-off of the solvent to obtain 29.9 g of a crude product. The crude product was purified by silica gel column chromatography with the use of an hexane/ethyl acetate (=2/1) mixture solvent and recrystallized from ethyl acetate to obtain 12.1 g of a pure product (yield: 38.2%).

Workup

  1. customAfter the reaction
  2. extractionfollowed by four times of extraction with 300 ml of ethyl acetate, three times
  3. washof washing with 500 ml of water
  4. dry with materialdrying with anhydrous magnesium sulfate and distilling-off of the solvent
  5. customto obtain 29.9 g of a crude product
  6. customThe crude product was purified by silica gel column chromatography with the use of an hexane/ethyl acetate (=2/1) mixture solvent
  7. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b89959a99ba64a849751348cdd3da701
Source dataset
uspto-grants-1992_05
Patent number
US05116530

Reaction notes

Loading…