Sodium hydride → 4-Cyclopropylmethoxy-benzenesulfonic acid sodium salt

HRID 1591688Notes

Reaction equation

HRID 1591688 reaction equation
[Na+:1].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([O-:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[H-].[Na+].Br[CH2:16][CH:17]1[CH2:19][CH2:18]1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[Na+:1].[CH:17]1([CH2:16][O:2][C:3]2[CH:8]=[CH:7][C:6]([S:9]([O-:12])(=[O:10])=[O:11])=[CH:5][CH:4]=2)[CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 4379756Sodium 4-hydroxybenzenesulfonate

Product 1

HCID 236871614-Cyclopropylmethoxy-benzenesulfonic acid sodium salt

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 75 g (323 mmol) of 4-hydroxybenzenesulfonic acid sodium salt in 1350 ml of DMF, 20.67 g (517 mmol) of 60% oil suspended NaH are carefully added portionwise at r.t. To the mixture, 11.93 g (32.3 mmol) of tetrabutylammonium iodide and 50.13 ml (517 mmol) of (bromomethyl)-cyclopropane are added successively. After stirring for 25 h at 60° C., the reaction mixture is cooled to r.t. Precipitates are collected and washed with CH2Cl2 several times, and then recrystalized with mixed solvent (EtOH:H2O=2:1) to give the title compound as a colorless solid.

Workup

  1. additionare carefully added portionwise at r.t
  2. temperaturethe reaction mixture is cooled to r.t
  3. customPrecipitates
  4. customare collected
  5. washwashed with CH2Cl2 several times
  6. customrecrystalized with mixed solvent (EtOH:H2O=2:1)

Sources & evidence

ORD record
ord-043653d6210d46fd893e578c68136e70
Source dataset
uspto-grants-2007_11
Patent number
US07291634B2

Reaction notes

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