p-Toluenesulfonic acid → 129969-30-8

HRID 1086631Notes

Reaction equation

HRID 1086631 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-bade03bf74ff4bb08859df4d4e05421a
Source dataset
uspto-grants-1991_07
Patent number
US05030736

Reaction notes

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