Ethanol → 5-(3-Methylphenyl)-2-thiophenecarboxylic acid

HRID 235101Notes

Reaction equation

HRID 235101 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([CH:13]=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C([OH:17])C>O.[N+]([O-])([O-])=O.[Ag+]>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[S:12][C:11]([C:13]([OH:17])=[O:14])=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 35871725-(3-Methylphenyl)-2-thiophenecarboxaldehyde

Product 1

HCID 105368035-(3-Methylphenyl)-2-thiophenecarboxylic acidYield 96%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 962WaterSolvent

Procedure

A solution of 5-(3-methylphenyl)-2-thiophenecarboxaldehyde (prepared immediately above, 4.7 g, 23.3 mmol) was dissolved in 100 mL of ethanol and sequentially treated with a solution of silver nitrate (7.9 g, 116.5 mmol) in 15 mL of water. The suspension was stirred at room temperature for 1 hour, then filtered, and the filter cake was washed with water and ether. The flitrate was separated, and the aqueous layer was acidified with conc. HCl to pH 4. This solution was twice extracted with ether. The extract was dried over MgSO4 and concentrated to give 4.6 g (96% yield) of 5-(3-methylphenyl)-2-thiophenecarboxylic acid. MS: 236 (M+NH4)+. NMR (CDCl3) d: 7.86 (d, 1H, J=5 Hz), 7.5-7.4 (m, 2H), 7.35-7.10 (m, 3H), 2.4 (s, 3H).

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with water and ether
  3. customThe flitrate was separated
  4. extractionThis solution was twice extracted with ether
  5. dry with materialThe extract was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9de8c63fe19f4601afc26fd19ee5a447
Source dataset
uspto-grants-1997_01
Patent number
US05597832

Reaction notes

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