Sodium Pyrosulfite → HCID 19423963, compound

HRID 743411Notes

Reaction equation

HRID 743411 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH:15]=[CH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H].S([O-])(O)=O.[Na+].S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C1C=CC=CC=1.C(O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Rh]>[Cl:23][C:19]1[CH:18]=[C:17]([CH2:16][CH2:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 656671Sodium PyrosulfiteHCID 23665763Sodium BisulfiteHCID 54207945HCID 54207945, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19423963HCID 19423963, compoundYield 98.5%

Reagents, catalysts & solvents 3

HCID 84599Chlorotris(triphenylphosphine)rhodium(I)CatalystHCID 241BenzeneSolventHCID 702EthanolSolvent

Procedure

5.4 g of this 2-benzyloxy-3'-chlorostilbene were treated with hydrogen in the presence of 300 mg of tris(triphenylphosphine)rhodium (I) chloride in a mixture of 60 ml of benzene and 40 ml ethanol at room temperature for one day. At the end of this time, aqueous sodium hydrogensulfite containing a small amount of sodium metabisulfite was added to the reaction mixture and allowed to react. Insoluble materials were removed by filtration. Ethyl acetate was added to the filtrate, and the mixture was washed once with water and twice with a saturated aqueous solution of sodium chloride. It was then dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 5.35 g (yield 98%) of benzyl 2-[2-(3-chlorophenyl)ethyl]phenyl ether.

Workup

  1. customto react
  2. customInsoluble materials were removed by filtration
  3. additionEthyl acetate was added to the filtrate
  4. washthe mixture was washed once with water and twice with a saturated aqueous solution of sodium chloride
  5. dry with materialIt was then dried over anhydrous sodium sulfate
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe resulting residue was purified by column chromatography through silica gel
  8. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-d5853cb163e24025aa1142b21a2f522a
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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