Chlorosulfonic acid → p-Tetradecylbenzenesulfonyl chloride

HRID 631077Notes

Reaction equation

HRID 631077 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-b9f40f13e1c94ec5aad2e719a61267d3
Source dataset
uspto-grants-2016_04
Patent number
US09320734B2

Reaction notes

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