Dimethylformamide → Sodium 2-(dodecanoyloxy)benzene-1-sulfonate

HRID 1274804Notes

Reaction equation

HRID 1274804 reaction equation
[CH:1]1[C:6](O)=[CH:5][CH:4]=[C:3]([S:8]([O-:11])(=[O:10])=[O:9])[CH:2]=1.[Na+:12].[C:13](Cl)(=[O:25])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CN(C)C=[O:30]>>[C:13]([O:25][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][C:3]=1[S:8]([O-:11])(=[O:10])=[O:9])(=[O:30])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[Na+:12]

Participants

4

Reactant 3

HCID 6228Dimethylformamide2×HCID 8166Dodecanoyl chlorideHCID 4379756Sodium 4-hydroxybenzenesulfonate

Product 1

HCID 23710196Sodium 2-(dodecanoyloxy)benzene-1-sulfonateYield 85%

Procedure

One-hundred grams of sodium p-phenolsulfonate which was previously dehydrated was dispersed in 300 g of dimethylformamide (hereinafter simply referred to as "DMF"), and lauroyl chloride at 50° C. was added dropwise to the above mixture over a period of 30 minutes while stirring with a magnetic stirrer. After completing the dropwise addition, the components were allowed to react with one another for 3 hours. Thereafter, the DMF was distilled off at 100° C. under a reduced pressure of 0.5 to 1 mmHg. After rinsing the resulting mixture with acetone, recrystallization was carried out in a water/acetone solvent (molar ratio 1:1), to give sodium lauroyloxybenzenesulfonate (yield 85%).

Workup

  1. customat 50° C.
  2. additionwas added dropwise to the above mixture over a period of 30 minutes
  3. additionthe dropwise addition
  4. customto react with one another for 3 hours
  5. distillationThereafter, the DMF was distilled off at 100° C. under a reduced pressure of 0.5 to 1 mmHg
  6. washAfter rinsing the resulting mixture
  7. customwith acetone, recrystallization

Sources & evidence

ORD record
ord-783d7d8278d1491782e2a42ccdecb42e
Source dataset
uspto-grants-2000_12
Patent number
US06159919

Reaction notes

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