Sulfuric Acid → HCID 13276468, compound

HRID 1388878Notes

Reaction equation

HRID 1388878 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH2:12]([OH:24])[CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].S(=O)(=O)(O)O>N1C=CC=CC=1>[S:7]([C:4]1[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=1)([O:24][CH2:12][CH2:13]/[CH:14]=[CH:15]\[CH2:16]/[CH:17]=[CH:18]\[CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 73974-Toluenesulfonyl chlorideHCID 10976130(3Z,6Z)-3,6-Dodecadien-1-ol

Product 1

HCID 13276468HCID 13276468, compoundYield 45.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 8.7 g (45 mmoles) of p-toluenesulfonyl chloride in 60 ml pyridine was added dropwise at 0°-5° C., a solution of 5.8 g (31.8 mmoles) of (Z,Z)-3,6-dodecadienol (T. Kajiwara, J. Sekiya, Y. Odake and A. Hatanaka, Agric. Biol. Chem., 41, 1481 (1977)). The temperature was allowed to rise to 25° C., and the reaction mixture was stirred at room temperature overnight. The resulting suspension was slowly poured into a mixture of 1 N aqueous sulfuric acid and ice and the product extracted with ether. The ether extracts were combined, washed with 10% sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent evaporated under reduced pressure. The residue (8.0 g) was chromatographed on a silica gel column. Elution with 1:1 hexane-ether gave 4.9 g (14.6 mmoles) (45.8%) of (Z,Z)-3,6-dodecadienyl tosylate, which was dissolved in 20 ml of acetone.

Workup

  1. customto rise to 25° C.
  2. extractionthe product extracted with ether
  3. washwashed with 10% sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue (8.0 g) was chromatographed on a silica gel column
  7. washElution with 1:1 hexane-ether

Sources & evidence

ORD record
ord-bc3cd9cc235649159e690a3a128e3b33
Source dataset
uspto-grants-1984_02
Patent number
US04434101

Reaction notes

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