p-Toluenesulfonic acid → 129969-30-8

HRID 2210270Notes

Reaction equation

HRID 2210270 reaction equation
[OH:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[O:12])[CH:8]=[C:9]([CH3:11])[CH3:10].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:11][C:9]1([CH3:10])[O:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7](=[O:12])[CH2:8]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 15643883HCID 15643883, compound

Product 1

HCID 15643884129969-30-8

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-hydroxy-2-(3-methyl-1-oxo-2-buten-1-yl) thiophene (39.0 g, 0.214 mol) and p-toluenesulfonic acid (3.5 g, 18 mmol) in toluene (400 mL) was heated to reflux for 3.5 d. The resultant solution was washed with saturated aqueous sodium bicarbonate and dried over sodium sulfate. The solvent was evaporated in vacuo to give a brown oil, 38.62 g (99%). A portion of the resultant oil was purified for analysis by distillation in a Kugelrohr oven at 145° to 155° C. at 0.35 mm Hg to give the product as an amber oil: IR (neat): 2979, 1664, 1530 and 1442 cm-1 ; MS: m/z 183 (MH+); 1H NMR (CDCl3): δ1.51 (s, 6H); 2.67 (s, 2H); 6.67 (d, J=5.4 Hz, 1H) and 7.60 (d, J=5.4 Hz, 1H).

Workup

  1. temperatureto reflux for 3.5 d
  2. washThe resultant solution was washed with saturated aqueous sodium bicarbonate
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated in vacuo
  5. customto give a brown oil, 38.62 g (99%)
  6. distillationA portion of the resultant oil was purified for analysis by distillation in a Kugelrohr oven at 145° to 155° C. at 0.35 mm Hg

Sources & evidence

ORD record
ord-05ba3ba82ff14232b46047d1e1a3f256
Source dataset
uspto-grants-1995_10
Patent number
US05457212

Reaction notes

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