Sulfuryl chloride → HCID 18352666, compound

HRID 429718Notes

Reaction equation

HRID 429718 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.S(Cl)([Cl:18])(=O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:18][CH:10]1[CH2:9][CH:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[CH3:1])[CH2:13][CH2:12][C:11]1=[O:14]

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 516892Sodium BicarbonateHCID 183526694-(2-Methylphenyl)cyclohexanone

Product 1

HCID 18352666HCID 18352666, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Prepared in analogy with a method in Hussey, A. S. and Herr, R. R., J. Org. Chem., 24, 843 (1959). To a 500 mL round-bottomed flask equipped with nitrogen inlet was added 33.3 grams (0.177 mol) of 4-(2-methylphenyl)cyclohexanone and 200 mL methylene chloride. To the stirring solution was added drop wise over 30 minutes a solution of 17.1 mL (0.212 mol) sulfuryl chloride in 10 mL methylene chloride. The reaction was stirred 14 hours at room temperature and poured into saturated aqueous sodium bicarbonate solution. The organic layer was separated, washed again with saturated aqueous sodium bicarbonate solution, dried over sodium sulfate, and evaporated to a yellow oil, 41 grams (100%), as a mixture of diastereomers which was used directly in the next step.

Workup

  1. customPrepared in analogy with a method in Hussey
  2. customTo a 500 mL round-bottomed flask equipped with nitrogen inlet
  3. customThe organic layer was separated
  4. washwashed again with saturated aqueous sodium bicarbonate solution
  5. dry with materialdried over sodium sulfate
  6. customevaporated to a yellow oil, 41 grams (100%), as a mixture of diastereomers which

Sources & evidence

ORD record
ord-663cd621717d4d1ba6a678bcc0e88a10
Source dataset
uspto-grants-2001_11
Patent number
US06319915B1

Reaction notes

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