Sulfuric Acid → HCID 20336687, compound

HRID 236861Notes

Reaction equation

HRID 236861 reaction equation
[CH3:1][C:2]([CH3:22])([CH2:18][CH2:19][CH2:20][CH3:21])[C:3](=[O:17])[CH:4]=[CH:5][O:6][S:7]([C:10]1[C:11]([CH3:16])=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:9])=[O:8].[I-:23].[Na+].[I-].[Li+].S(=O)(=O)(O)O>CC(C)=O.C(Cl)(Cl)Cl>[CH3:1][C:2]([CH3:22])([CH2:18][CH2:19][CH2:20][CH3:21])[C:3](=[O:17])/[CH:4]=[CH:5]/[I:23].[CH3:1][C:2]([CH3:22])([CH2:18][CH2:19][CH2:20][CH3:21])[C:3](=[O:17])[CH:4]=[CH:5][O:6][S:7]([C:10]1[C:11]([CH3:16])=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:9])=[O:8]

Participants

8

Reactant 4

HCID 1118Sulfuric AcidHCID 5238Sodium IodideHCID 66321Lithium iodideHCID 73769827HCID 73769827, compound

Product 2

HCID 20336687HCID 20336687, compoundHCID 73769827HCID 73769827, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6212ChloroformSolvent

Procedure

The sample of (25A) was dissolved in 250 ml of dry acetone and stirred overnight under argon with 25.2 g of sodium iodide and 1.0 g of lithium iodide. The (CHCl3) analysis the next day of the reaction mixture showed little or no reaction had taken place. A 0.25 ml portion of concentrated sulfuric acid was added to the dark colored reaction mixture and it was then heated to reflux using an oil bath. The mixture rapidly became very viscous and the analysis after a few minutes showed considerable amounts of (27A) had formed at the expense of (25A). After 1 hour of reflux the resultant very dark colored reaction mixture was evaporated in vacuo. The residue was mixed with ether and washed with aqueous sodium thiosulfate and then with saturated aqueous sodium bicarbonate. The resultant extract was dried (MgSO4) and evaporated in vacuo. The resultant 27.8 g of residue was distilled in vacuo to yield 18.7 g of (27A) as a yellow oil, bp 78°-88° (0.2 mm); Rf (CHCl3) 0.58; nmr (CDCl3) δ 0.90 (3H, broad t, J=6.0 Hz), 1.14 (6H, s), 1.0-1.8 (6H, m) 7.66 (1H, d, J=14.8 Hz) and 8.07 ppm (1H, d, J=14.8 Hz); ir (film) 940, 1040, 1080, 1470, 1560, 1688, 2860, 2930 and 2960 cm-1.

Workup

  1. temperaturewas then heated
  2. temperatureto reflux
  3. waitthe analysis after a few minutes showed considerable

Sources & evidence

ORD record
ord-d10962be56e246b2a41e2c7bf4e1f009
Source dataset
uspto-grants-1979_06
Patent number
US04158018

Reaction notes

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