Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-Phenoxybut-2-yn-1-ol

HRID 1607818Notes

Reaction equation

HRID 1607818 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1CCCCC1[O:24][CH2:25][C:26]#[C:27][CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(O)C>[O:29]([CH2:28][C:27]#[C:26][CH2:25][OH:24])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19849494HCID 19849494, compound

Product 1

HCID 160466794-Phenoxybut-2-yn-1-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
55 °C

Procedure

1.02 g (0.004 mol) of pyridinium p-toluenesulfonate was added to a solution of 2 g of 4-phenoxy-but-2-yn-1-ol tetrahydropyranyl ether in 20 ml of 96% ethanol. The reaction mixture was stirred for 2 hours at 55° C.; the solvent was then removed in vacuo and the residue diluted with 20 ml of water and extracted with methylene chloride (3×20 ml). The combined extracts were dried over sodium sulfate and the solvent evaporated in vacuo. The residue was purified by column chromatography on 30 g of silica gel, using hexane-ethyl acetate (90:10) as eluant, to yield 4-phenoxy-but-2-yn-1-ol, as an oil.

Workup

  1. customthe solvent was then removed in vacuo
  2. additionthe residue diluted with 20 ml of water
  3. extractionextracted with methylene chloride (3×20 ml)
  4. dry with materialThe combined extracts were dried over sodium sulfate
  5. customthe solvent evaporated in vacuo
  6. customThe residue was purified by column chromatography on 30 g of silica gel

Sources & evidence

ORD record
ord-a74255ee3cee4ee981c5aed6093589c3
Source dataset
uspto-grants-1989_09
Patent number
US04867915

Reaction notes

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