Sodium hydride → 4-Cyclopropylmethoxy-benzenesulfonic acid sodium salt

HRID 2216651Notes

Reaction equation

HRID 2216651 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-8221700016e944c2bb05b708bb96d41d
Source dataset
uspto-grants-2006_09
Patent number
US07112611B2

Reaction notes

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