p-Toluenesulfonic acid → HCID 18976425, compound

HRID 2393582Notes

Reaction equation

HRID 2393582 reaction equation
[Br:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([CH2:10][CH2:11][CH2:12][CH:13]2OCCCO2)[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(OCC)(=O)C.CCCCCC>C(O)C.O1CCOCC1>[Br:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]2[C:5](=[C:6]([O:8][CH3:9])[CH:7]=1)[CH:13]=[CH:12][CH2:11][CH2:10]2

Participants

7

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 8058HexaneHCID 8857Ethyl AcetateHCID 18976450HCID 18976450, compound

Product 1

HCID 18976425HCID 18976425, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 1.10 gm (3.19 mmol) of 2-[3-(3-bromo-2,5-dimethoxyphenyl)propyl]-1,3-dioxane and 300 mg p-toluene sulphonic acid in 10 ml absolute ethanol was refluxed for 48 hours at which time tlc analysis (silica gel, 1:4 ethyl acetate:hexane) indicated the absence of the dioxane. The solvent was removed in vacuo and the residue was partitioned between ether and 5% sodium carbonate. The ether extract was washed with brine, dried with Na2SO4, filtered and the solvent was removed in vacuo. The residue was kugelrohr distilled at 0.005 mm Hg to give 0.85 gm (99%) of a colorless oil, bp 95° C. (air bath temperature), homogeneous by tlc (ibid), Rf 0.74.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between ether and 5% sodium carbonate
  3. extractionThe ether extract
  4. washwas washed with brine
  5. dry with materialdried with Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. distillationThe residue was kugelrohr distilled at 0.005 mm Hg

Sources & evidence

ORD record
ord-f78a599adbe844ceae63a7ba457632a6
Source dataset
uspto-grants-1998_09
Patent number
US05807897

Reaction notes

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