p-Toluenesulfonic acid → HCID 86587289, compound

HRID 580799Notes

Reaction equation

HRID 580799 reaction equation
[CH3:1][O:2][CH:3](OC)[CH2:4][C:5]([O:7][CH2:8][O:9][C:10](=[O:17])[CH2:11][CH:12](OC)[O:13][CH3:14])=[O:6].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:14][O:13][CH:12]=[CH:11][C:10]([O:9][CH2:8][O:7][C:5](=[O:6])[CH:4]=[CH:3][O:2][CH3:1])=[O:17]

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86587290HCID 86587290, compound

Product 1

HCID 86587289HCID 86587289, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Methylene bis(3,3-dimethoxypropionate) (14.01 g, 50 mmol) prepared as described in Example 19 and a catalytic amount of p-toluene sulfonic acid is added to toluene (250 ml). The methanol is removed by warming the reaction under an N2 atmosphere. When the reaction is complete the toluene is distilled off under reduced pressure. Diethyl ether (250 ml) is added and the mixture is washed with saturated aqueous sodium hydrogen carbonate (5×50 ml) and water (3×50 ml). The organic layer is dried (MgSO4) before evaporation to give 8.52 g (79%) product. 1H NMR (300 MHz, CDCl3): δ 3.65 (2×CH3, s), 5.2 (2×CH, d), 5.8 (O--CH2 --O), 7.65 (2×CH2, d).

Workup

  1. customThe methanol is removed
  2. temperatureby warming
  3. customthe reaction under an N2 atmosphere
  4. distillationis distilled off under reduced pressure
  5. additionDiethyl ether (250 ml) is added
  6. washthe mixture is washed with saturated aqueous sodium hydrogen carbonate (5×50 ml) and water (3×50 ml)
  7. dry with materialThe organic layer is dried (MgSO4)
  8. custombefore evaporation

Sources & evidence

ORD record
ord-e889229287e04829bd12aac62f690696
Source dataset
uspto-grants-1999_07
Patent number
US05919753

Reaction notes

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