Sulfuric Acid → HCID 58174739, compound

HRID 1259468Notes

Reaction equation

HRID 1259468 reaction equation
[S:1](=[O:5])(=O)([OH:3])[OH:2].[CH:6]1([P:12]([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:13]2[CH2:18][CH2:17][CH:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>O>[CH:25]1([P:12]([CH:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]2)[CH:13]2[CH2:14][CH2:15][CH:16]([C:19]3[CH:20]=[CH:21][C:22]([S:1]([OH:3])(=[O:5])=[O:2])=[CH:23][CH:24]=3)[CH2:17][CH2:18]2)[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 58174777HCID 58174777, compound

Product 1

HCID 58174739HCID 58174739, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Sulfuric acid (96 percent, 200 mL) is added slowly under nitrogen to dicyclohexyl(4-phenylcyclohexyl)phosphine (25 g; 70.2 mol), prepared above, at −70° C. The mixture is warmed to room temperature and stirred for 3 hrs. The reaction mixture is added carefully to 2 L of water purged with nitrogen and cooled to about +5° C. The water solution is extracted 4 times with methylene chloride (250 mL each, four times). The solid present initially in the water solution disappears during the course of extraction. Methylene chloride is evaporated, a white residue is dried in vacuum for 1 h to give 25.1 g (82%) of the product 4-[4-(dicyclohexylphosphino)cyclohexyl]benzenesulfonate in the acid form, Cy2PC6H10C6H4SO3H. 31P{1H} NMR (δ CD2Cl2, ppm): 13.07; 1H NMR (δ CD2Cl2, ppm): 1.2-2.2 (m, 31H, cyclohexyl), 2.60 (m, 1H, PhCH), 7.24 and 7.59 (dd, J=8.2 Hz, 4H, aromatic).

Workup

  1. customprepared above, at −70° C
  2. custompurged with nitrogen
  3. temperaturecooled to about +5° C
  4. extractionThe water solution is extracted 4 times with methylene chloride (250 mL each, four times)
  5. extractionThe solid present initially in the water solution disappears during the course of extraction
  6. customMethylene chloride is evaporated
  7. customa white residue is dried in vacuum for 1 h

Sources & evidence

ORD record
ord-bbd51f8f6c3e4e17aa99132d0c606d05
Source dataset
uspto-grants-2013_06
Patent number
US08466306B2

Reaction notes

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