p-Toluenesulfonic acid → (E)-4-methyl-3,5-dioxa-7-decen-9-yne

HRID 1106004Notes

Reaction equation

HRID 1106004 reaction equation
[CH:1](/[OH:6])=[CH:2]\[CH2:3][C:4]#[CH:5].[CH:7]([O:9][CH2:10][CH3:11])=[CH2:8].C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOCC>[CH3:8][CH:7]([O:6][CH2:1]/[CH:2]=[CH:3]/[C:4]#[CH:5])[O:9][CH2:10][CH3:11]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8023Ethyl vinyl etherHCID 574516562-trans-Penten-4-ynol

Product 1

HCID 12821656(E)-4-methyl-3,5-dioxa-7-decen-9-yne

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The 2-trans-penten-4-yn-1-ol (47.7 g) was dissolved in ether (50 ml), cooled to 0° and treated with ethyl vinyl ether (50 mL). To this solution, solid p-toluene sulfonic acid (0.1 g) was added and after a slight exothermic reaction, the mixture was stirred for a further 20 min and quenched with triethylamine (2 mL). The solvents were removed in vacuo and the residue was dissolved in ether, washed with aqueous NaHCO3 solution, dried (MgSO4) and concentrated. The residue was purified by liquid chromatography (two columns, 6:1 parts by volume hexane-ethyl acetate) and distilled, bp 88°-98° (26 mmHg) to give (E)-4-methyl-3,5-dioxa-7-decen-9-yne.

Workup

  1. temperaturecooled to 0°
  2. customafter a slight exothermic reaction
  3. customquenched with triethylamine (2 mL)
  4. customThe solvents were removed in vacuo
  5. dissolutionthe residue was dissolved in ether
  6. washwashed with aqueous NaHCO3 solution
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customThe residue was purified by liquid chromatography (two columns, 6:1 parts by volume hexane-ethyl acetate)
  10. distillationdistilled

Sources & evidence

ORD record
ord-7171187a4e364c268a8c7bfb1ab06cb9
Source dataset
uspto-grants-1982_01
Patent number
US04311645

Reaction notes

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