(Z)-2-Carbomethoxy-3-phenyl-2-propene-1-sulfonic Acid Sodium Salt → 2-Carbomethoxy-3-phenylpropane-1-sulfonic Acid Sodium Salt

HRID 1197500Notes

Reaction equation

HRID 1197500 reaction equation
[Na+:1].[C:2](/[C:6](=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)/[CH2:7][S:8]([O-:11])(=[O:10])=[O:9])([O:4][CH3:5])=[O:3].[H][H]>[Ni].CO.O>[Na+:1].[C:2]([CH:6]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[CH2:7][S:8]([O-:11])(=[O:10])=[O:9])([O:4][CH3:5])=[O:3]

Participants

5

Reactant 2

HCID 88128861(Z)-2-Carbomethoxy-3-phenyl-2-propene-1-sulfonic Acid Sodium SaltHCID 178418361HCID 178418361, compound2×

Product 1

HCID 881293232-Carbomethoxy-3-phenylpropane-1-sulfonic Acid Sodium SaltYield 88%

Reagents, catalysts & solvents 2

HCID 935NickelCatalyst2×HCID 22242641Methanol--water (1/1)Solvent

Procedure

To the 8 L of 1:1 methanol/water mixture containing the resultant compound from Example 1C was added 60 g of W-24 raney nickel. The resulting suspension was pressurized under 50 psi of hydrogen and was allowed to shake on a Parr shaker for 24 hours, at which time an additional 20 g of raney nickel catalyst was added. After 6 hours under 50 psi of hydrogen, the catalyst was removed by filtration and the solution was concentrated to dryness. To the dry white solid, ethyl acetate (6 L) and heptane (4 L) were added and the solution was vigorously stirred with a mechanical stirrer overnight. The white suspended solid was removed by filtration yielding 530 g (88%) of the desired product as an amorphous powder that was contaminated with approximately one equivalent of sodium bromide. The compound was used without any additional purification: IR (KBr) 1740, 1215, 1050 cm-1. 1H NMR (DMSO-d6, 300 MHz) δ 2.48-2.54 (m, 1H), 2.74-2.87 (m, 2H), 2.91-3.04 (m, 2H), 3.48 (s, 3H), 7.12-7.32 (m, 5H); 13C NMR (75 MHz, D2O/DMSO-d6) δ38.18, 44.80, 52.67, 52.82, 127.42, 129.13, 129.34, 138.14, 176.84.

Workup

  1. customthe catalyst was removed by filtration
  2. concentrationthe solution was concentrated to dryness
  3. additionTo the dry white solid, ethyl acetate (6 L) and heptane (4 L) were added
  4. customwas removed by filtration

Sources & evidence

ORD record
ord-c72e01cc11864add84ea65fd6e61bb31
Source dataset
uspto-grants-1994_01
Patent number
US05275950

Reaction notes

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