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

HRID 1729258Notes

Reaction equation

HRID 1729258 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 h, at which time an additional 20 g of raney nickel catalyst was added. After 6 h under 50 psi of hydrogen, the catalyst was removed by filtration and the solution was concentrated to dryness. To the dry white solid was added ethyl acetate (6 L) and heptane (4 L) and the solution was vigorously stirred with a mechanical stirrer overnight. The white suspension was removed by filtration yielding 530 g (88%) of the desired product as an amorphous powder that was contaminated with approximately one equivalent of NaBr. The compound was used without any additional purification: IR (KBr) 1740, 1215, 1050 cm-1. 1H NMR (DMSO D-6) 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 D-6) δ 38.18, 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 was added ethyl acetate (6 L) and heptane (4 L)
  4. customThe white suspension was removed by filtration

Sources & evidence

ORD record
ord-f24f585bf91748ba901bf965afdad90c
Source dataset
uspto-grants-1994_07
Patent number
US05332742

Reaction notes

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