4-Toluenesulfonyl chloride → Benzenesulfonic acid, 4-methyl-, dodecyl ester

HRID 1166011Notes

Reaction equation

HRID 1166011 reaction equation
[CH2:1]([OH:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C(N(CC)CC)C.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>ClCCl>[S:27]([C:24]1[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=1)([O:13][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:29])=[O:28]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 81931-DodecanolHCID 8471Triethylamine

Product 1

HCID 82417Benzenesulfonic acid, 4-methyl-, dodecyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred and a cooled solution of lauryl alcohol (186.0 g, 1.0 mole) and triethyl amine (121.0 g, 1.2 mole) in dichloromethane (600 ml), p-toluene sulphonyl chloride (228.0 g, 1.2 mole) in dichloromethane (400 ml) was slowly added and the reaction was continued at room temperature for 10 hours. The reaction mixture was then washed with 20% sodium chloride solution (500 ml). The washed organic layer was dried over anhydrous sodium sulphate. Removal of solvent under vacuo resulted in colorless oil that solidified on keeping to yield lauryl tosylate. (309.0 g, 91%), m. p. 29° C. (literature m. p. 29° C.).

Workup

  1. washThe reaction mixture was then washed with 20% sodium chloride solution (500 ml)
  2. dry with materialThe washed organic layer was dried over anhydrous sodium sulphate
  3. customRemoval of solvent under vacuo
  4. customresulted in colorless oil that

Sources & evidence

ORD record
ord-648c7f6b770c4fe780d8129ffd23db80
Source dataset
uspto-grants-2003_09
Patent number
US06613340B2

Reaction notes

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