Sodium Carbonate → HCID 22678452, compound

HRID 1837706Notes

Reaction equation

HRID 1837706 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH2:11]O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:19])=O.C(=O)([O-])[O-].[Na+].[Na+].[C:27]1([P:33]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=CC=CC=1.CN(C)C=O.C(#N)C.C(OCC)(=O)C>[Cl-:19].[CH:1]1([CH2:7][O:8][C:9]2[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=2[CH2:11][P+:33]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 24386Thionyl ChlorideHCID 28562709HCID 28562709, compound

Product 1

HCID 22678452HCID 22678452, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

3.06 g of 2-(cyclohexylmethyloxy)benzyl alcohol was dissolved in 30 ml of toluene, 1.52 ml of thionyl chloride and 5 drops of N,N-dimethylformamide were added thereto and the mixture was stirred for 70 minutes under ice-cooling. An aqueous sodium carbonate was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. The solution was filtered through alumina, and the solvent was evaporated, to give a slight yellow oil. The oil was dissolved in 3 ml of acetonitrile, 3.65 g of triphenylphosphine was added thereto, and the mixture was stirred at 110° C. for one hour and 45 minutes. Ethyl acetate was added to the reaction solution and the product was collected by filtration, to give 6.51 g of the title compound as a white powder.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered through alumina
  6. customthe solvent was evaporated
  7. customto give a slight yellow oil
  8. stirringthe mixture was stirred at 110° C. for one hour and 45 minutes
  9. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-b27dc9bc79864d2c830362ba7b5edfd3
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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