Chlorosulfonic acid → p-Tetradecylbenzenesulfonyl chloride

HRID 1966914Notes

Reaction equation

HRID 1966914 reaction equation
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]CCCC)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:25][S:26](O)(=[O:28])=[O:27]>C(Cl)(Cl)Cl>[CH2:7]([C:1]1[CH:6]=[CH:5][C:4]([S:26]([Cl:25])(=[O:28])=[O:27])=[CH:3][CH:2]=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 78187Benzene, octadecyl-

Product 1

HCID 15715900p-Tetradecylbenzenesulfonyl chlorideYield 68%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-phenyloctadecane (0.69 g, 2.5 mmol) in CHCl3 (5 mL) was added chlorosulfonic acid (0.5 mL, 7.5 mmol) and the mixture was stirred at rt for 22 h. The mixture was poured on ice and extracted with CH2Cl2. The combined extracts were washed with water, a solution of NaHCO3, and water, dried (Na2SO4), and concentrated in vacuo. The residue was chromatographed on silica gel (70-230 mesh) with hexane/ethyl acetate (49:1) to give the product as a white solid (0.63 g, 1.7 mmol, 68%), mp 32-33° C.; 1H NMR (300 MHz, CDCl3) δ 0.88 (t, 3H, J=7.2 Hz), 1.25 (m, 22H), 1.65 (m, 2H), 2.72 (t, 2H, J=7.8 Hz), 7.42 (d, 2H, J=8.4 Hz), 7.93 (d, 2H, J=8.4 Hz); 13C NMR (75 MHz, CDCl3) 14.1, 22.6, 29.1, 29.3, 29.5, 29.6, 29.7, 30.9, 31.9, 36.0, 126.9, 129.5, 141.7, 151.6.

Workup

  1. additionThe mixture was poured on ice
  2. extractionextracted with CH2Cl2
  3. washThe combined extracts were washed with water
  4. dry with materiala solution of NaHCO3, and water, dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (70-230 mesh) with hexane/ethyl acetate (49:1)

Sources & evidence

ORD record
ord-73a6e6bd24564b809dfe374344563614
Source dataset
uspto-grants-2013_04
Patent number
US08420678B2

Reaction notes

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