Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 10877568, compound

HRID 2352501Notes

Reaction equation

HRID 2352501 reaction equation
[CH3:1][Si:2]([CH3:17])([CH3:16])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9]C1CCCCO1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[CH3:17][Si:2]([CH3:1])([CH3:16])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 14652360HCID 14652360, compound

Product 1

HCID 10877568HCID 10877568, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-Trimethylsilyl[6-(oxacyclohex-2-yloxy)]hex-1-yne (76 g, 300 mmol) and pyridinium p-toluenesulfonate (0.05 g) were heated at reflux in methanol (200 mL). After cooling the solvent was removed under reduced pressure, the residue was dissolved in methylene chloride and washed with water, brine and dried (MgSO4). Evaporation of the solvent under reduced pressure afforded a residue which was distilled (b.p. 96° C., 3 mm Hg) to give 37.6 g (64%) of the product.

Workup

  1. temperatureAfter cooling the solvent
  2. customwas removed under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customEvaporation of the solvent under reduced pressure
  7. customafforded a residue which
  8. distillationwas distilled (b.p. 96° C., 3 mm Hg)

Sources & evidence

ORD record
ord-bd69a0667ac1498f804d7bed6fd4d07d
Source dataset
uspto-grants-1989_10
Patent number
US04877779

Reaction notes

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