HCID 86651762, compound → HCID 23722193, compound

HRID 1945173Notes

Reaction equation

HRID 1945173 reaction equation
[H][H].[CH:3]1([P:9]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)([CH:11]2[CH2:16][CH2:15][CH2:14][CH:13]([S:17]([O-:20])(=[O:19])=[O:18])[CH2:12]2)=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Na+:27].C1(P(C2CCCCC2)(C2CCCC(S(OCC)(=O)=O)C2)=O)CCCCC1>CO>[C:21]1([P:9]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)([C:11]2[CH:12]=[C:13]([S:17]([O-:20])(=[O:19])=[O:18])[CH:14]=[CH:15][CH:16]=2)=[O:10])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1.[Na+:27]

Participants

5

Reactant 3

HCID 86651762HCID 86651762, compoundHCID 86651763HCID 86651763, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23722193HCID 23722193, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

DPPOBS-Na (7.0 g; 18.4 mmoL), prepared as above, is dissolved in dry methanol (70 mL) and placed into a Parr reactor (150 mL) containing 7 g of catalyst comprising Ru (5 wt percent) on carbon. Hydrogenation is carried out at 1,000 psi (6,895 kPa) hydrogen and at 100° C. The reaction is monitored by 31P and 1H NMR. After 2 weeks, resonances for the aromatic protons in the 1H NMR spectrum disappear, and new resonances appear in the 31P NMR spectrum. The mixture is filtered; a black solid on the filter is washed with methanol. The solvent is evaporated, and the residue is dried in vacuum to give a white solid identified as sodium 3-(dicyclohexylphosphinyl)cyclohexane-1-sulfonate (DCHPOCHS-Na). Yield 4.0 g (55%). 31P{1H} NMR (CD3OD, ppm): 5.68 (major, ca. 87%) and 57.99 (minor, ca. 13%). (3) Step 3 of Example 1 is repeated using the intermediate product from step (2) of this example. Subsequently, steps 4 to 6 of Example 1 are also reproduced to yield Ligand 1 of this invention, namely, the sodium salt of 3-(dicyclohexylphosphino)cyclohexane-1-sulfonic acid.

Workup

  1. waitAfter 2 weeks
  2. filtrationThe mixture is filtered
  3. washa black solid on the filter is washed with methanol
  4. customThe solvent is evaporated
  5. customthe residue is dried in vacuum
  6. customto give a white solid

Sources & evidence

ORD record
ord-689bb0ccd6ef4fcc939ec29d7286d5fa
Source dataset
uspto-grants-2013_03
Patent number
US08394978B2

Reaction notes

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