4-Chlorobenzenesulfonyl chloride → n-Eicosanyl-4-chlorobenzenesulphonate

HRID 1377380Notes

Reaction equation

HRID 1377380 reaction equation
[CH2:1]([OH:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][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][CH3:20].C(N(CC)CC)C.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>C(Cl)Cl>[CH2:1]([O:21][S:36]([C:33]1[CH:34]=[CH:35][C:30]([Cl:29])=[CH:31][CH:32]=1)(=[O:38])=[O:37])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][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][CH3:20]

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 124041-Eicosanol

Product 1

HCID 54562082n-Eicosanyl-4-chlorobenzenesulphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred solution of eicosanol (5.0 g, 16.70 mmol) and triethylamine (4 ml) in methylene chloride (80 ml) was added dropwise a solution of 4-chlorobenzene-sulphonyl chloride (3.90 g, 18.50 mmol) in methylene chloride (20 ml) and this solution was stirred for 24 h. The reaction mixture was then diluted with more methylene chloride (100 ml) and washed with water (2×75 ml). The organic layer was dried over MgSO4, filtered and concentrated to give a crude product which was recrystallized from methanol to give n-eicosanyl-4-chlorobenzenesulphonate the product (5.10 g, 65%) m.p. 69°-70° C. max; 3000-2800, 1367, 1184, 1176, 963 cm-1. m/z, 472 (M+). Found C, 66.16%; H 9.75%; S, 6.74% Cl, 7.40% C26H45O3SCl requires C, 66.00%; H, 9.59%; S, 6.78%; Cl, 7.49%. 1Hnmr, 0.855 (t, J-6.6 Hz, 3H); 1.10-1.65 (m); 4.030 (t, J=6.4 Hz, 2H); 7.48-7.53 (m, 2H); 7.80-7.84 (m, 2H).

Workup

  1. washwashed with water (2×75 ml)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a crude product which
  6. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-c665ee17f0954718bba09b7b4ce3cc09
Source dataset
uspto-grants-1997_09
Patent number
US05665328

Reaction notes

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