p-Toluenesulfonic acid → HCID 19016910, compound

HRID 1728964Notes

Reaction equation

HRID 1728964 reaction equation
[Si]([C:5]1[CH:6]=[C:7]([Si:11]([CH3:16])([CH3:15])[O:12]C#C)[CH:8]=[CH:9][CH:10]=1)(C)(C)C.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20](S(O)(=O)=O)=[CH:19][CH:18]=1.[CH:28]#[CH:29]>C1C=CC=CC=1>[C:22]([C:17]1[CH:27]=[C:16]([Si:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:28]#[CH:29])[CH:6]=2)([CH3:15])[O:12][Si:11]([CH3:16])([CH3:15])[CH3:7])[CH:20]=[CH:19][CH:18]=1)#[CH:21]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6326AcetyleneHCID 67691590HCID 67691590, compound

Product 1

HCID 19016910HCID 19016910, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The above-described ethynyl silanol (5.0 g, 0.028 mol) from Example 4 was dissolved in dry benzene (40 mL) and a trace of p-toluene sulfonic acid was added. The reaction was refluxed for 4 hours. Gas chromatographic analysis of the reaction mixture showed the condensation to be complete. The solution was washed well with water, dried over sodium sulfate, concentrated, and distilled at reduced pressure to give a pale yellow liquid (b.p. 125° C./0.01 torr, 4.2 g, 88% yield). Differential scanning calorimetric analysis of this liquid showed the characteristic exotherm of acetylene polymerization at 180° to 250° C. The heat of reaction was 70 calories/gram. The liquid had the following spectral characteristics:

Workup

  1. temperatureThe reaction was refluxed for 4 hours
  2. customthe condensation
  3. washThe solution was washed well with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. distillationdistilled at reduced pressure
  7. customto give a pale yellow liquid (b.p. 125° C./0.01 torr, 4.2 g, 88% yield)

Sources & evidence

ORD record
ord-9dfac3ebc4a24d6f9964640c32c8fbfe
Source dataset
uspto-grants-1994_07
Patent number
US05329036

Reaction notes

Loading…