Water → HCID 53657895, compound

HRID 1164770Notes

Reaction equation

HRID 1164770 reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].[C:5]1(C)[CH:10]=[CH:9][C:8]([S:11](O)(=O)=O)=[CH:7][CH:6]=1.[OH2:16]>>[OH:16][C:5]1[CH:6]=[CH:7][C:8]([S:11][C@H:2]([CH3:3])[C:1]([O:4][CH2:1][CH2:2][CH3:3])=[O:4])=[CH:9][CH:10]=1

Participants

4

Reactant 3

HCID 962WaterHCID 10311-PropanolHCID 6101p-Toluenesulfonic acid

Product 1

HCID 53657895HCID 53657895, compoundYield 83%

Procedure

A solution of HPTPA (0.06 mole, 11 g) in an molar excess of 1-propanol (45 ml), containing a crystal of p-toluene sulphonic acid, was heated at reflux while allowing water to distil from the reaction mix. When no acid remained, as shown by IR-spectroscopy, the excess solvent was allowed to distil out and the cold residue taken into ether and washed with saturated NaHCO3 solution, dried (MgSO4) and the crude product isolated by evaporation. This was purified by distillation under reduced pressure (yield: 83%; SOR: +98°,c=2). The properties of the product determined by IR, 1H-NMR and mass spectroscopy and elemental analysis were consistent with the assigned structure.

Workup

  1. temperaturewas heated
  2. temperatureat reflux
  3. customto distil from the reaction
  4. additionmix
  5. customto distil out
  6. washwashed with saturated NaHCO3 solution
  7. dry with materialdried (MgSO4)

Sources & evidence

ORD record
ord-e580d6430e7b4a2685bd70c768ab2cad
Source dataset
uspto-grants-1990_03
Patent number
US04906402

Reaction notes

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