Cyclohexane, (bromomethyl)- → Cyclohexylmethylsulfonate sodium salt

HRID 264006Notes

Reaction equation

HRID 264006 reaction equation
[S:1](=[O:4])([OH:3])[O-:2].[Na+:5].[CH:6]1([CH2:12]Br)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1>O>[Na+:5].[CH:6]1([CH2:12][S:1]([O-:3])(=[O:2])=[O:4])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 137636Cyclohexane, (bromomethyl)-HCID 23665763Sodium Bisulfite

Product 1

HCID 23693649Cyclohexylmethylsulfonate sodium saltYield 39.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of sodium bisulfite (32 g, 307 mmole) in H2O (200 mL) was added cyclohexylmethyl bromide (21 mL, 150 mmole). The mixture was then stirred vigorously while heated at reflux for 48 hours. Upon cooling to room temperature, a white precipitate formed. The precipitate was collected on a Buchner funnel and washed with diethyl ether to wash away residual cyclohexylmethyl bromide. The white plate-like solid was dried under high vacuum overnight to provide 11.8 g (39%) of the title compound which had a m.p. >400° C.

Workup

  1. temperaturewhile heated
  2. temperatureat reflux for 48 hours
  3. customa white precipitate formed
  4. customThe precipitate was collected on a Buchner funnel
  5. washwashed with diethyl ether
  6. washto wash away residual cyclohexylmethyl bromide
  7. customThe white plate-like solid was dried under high vacuum overnight

Sources & evidence

ORD record
ord-d0cb1adc8cf942d58ef2e2649c9ee2b1
Source dataset
uspto-grants-1997_07
Patent number
US05646165

Reaction notes

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