Cyclohexane, (bromomethyl)- → Cyclohexylmethylsulfonate sodium salt

HRID 1955607Notes

Reaction equation

HRID 1955607 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-00beb5e4cd66468286406f2f0a7deda1
Source dataset
uspto-grants-1998_07
Patent number
US05776927

Reaction notes

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