p-Toluenesulfonic acid → HCID 86587289, compound

HRID 260625Notes

Reaction equation

HRID 260625 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 (a) above 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-c5597f3015234e1ea0b530f74d09e5e4
Source dataset
uspto-grants-1996_06
Patent number
US05529766

Reaction notes

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