Water → Sodium (2,6-dimethylphenyl)methanesulfonate

HRID 2252369Notes

Reaction equation

HRID 2252369 reaction equation
[S:1]([O-:4])([O-:3])=[O:2].[Na+:5].[Na+].Cl[CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][CH:12]=[CH:11][C:10]=1[CH3:16].O.[Cl-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[Na+:5].[CH3:16][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]([CH3:15])[C:9]=1[CH2:8][S:1]([O-:4])(=[O:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 5234Sodium ChlorideHCID 24437Sodium SulfiteHCID 2211542,6-Dimethylbenzyl Chloride

Product 1

HCID 87608575Sodium (2,6-dimethylphenyl)methanesulfonateYield 88%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Sodium sulfite (442.4 g) was added to a stirred mixture of 2-chloromethyl-1,3-dimethyl-benzene (526.6 g), tetrabutylammonium iodide (6.4 g) and water (3.0 L). The mixture was warmed to reflux for 1 h. As the mixture cooled to room temperature, sodium chloride (526 g) and ethyl acetate (1.4 I) were added. The mixture was stirred and cooled to <10° C. The product was collected by filtration and washed with ethyl acetate (250 mL) and acetone (500 mL). The product was dried in vacuo at 60° C. to constant weight to give (2,6-dimethyl-phenyl)-methanesulfonic acid sodium salt (634 g, 88%). 1H NMR (300 MHz, DMSOd6): δ 7.17-6.91 (m, 3H, ArH), 3.96 (s, 2H, CH2), and 2.29 (s, 6H, CH3).

Workup

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for 1 h
  3. temperaturecooled to <10° C
  4. filtrationThe product was collected by filtration
  5. washwashed with ethyl acetate (250 mL) and acetone (500 mL)
  6. customThe product was dried in vacuo at 60° C. to constant weight

Sources & evidence

ORD record
ord-ad736597062349aab11df244d06ef137
Source dataset
uspto-grants-2008_01
Patent number
US07321061B2

Reaction notes

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