Aluminum(III) Chloride → Ethyl 8-methyl-2,3-dihydrobenz-1,4-oxathiin-7-carboxylate

HRID 582823Notes

Reaction equation

HRID 582823 reaction equation
CS([S:5][CH2:6][CH2:7][O:8][C:9]1[C:10]([CH3:20])=[C:11]([CH:17]=[CH:18][CH:19]=1)[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=O)=O.[Cl-].[Cl-].[Cl-].[Al+3]>[N+](C)([O-])=O>[CH3:20][C:10]1[C:9]2[O:8][CH2:7][CH2:6][S:5][C:19]=2[CH:18]=[CH:17][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13]

Participants

4

Reactant 2

HCID 6451240Aluminum(III) ChlorideHCID 15376196Ethyl 3-(2-methylsulfonylthioethoxy)-2-methylbenzoate

Product 1

HCID 15376197Ethyl 8-methyl-2,3-dihydrobenz-1,4-oxathiin-7-carboxylate

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

1.0 g (3.4 mmol) of ethyl 3-(2-methylsulfonylthioethoxy)-2-methylbenzoate are dissolved in 5 ml of nitromethane. 0.42 g (3.14 mmol) of aluminum trichloride is added. The mixture is stirred for 45 minutes at room temperature. Working-up is carried out by adding 10 ml of 2 N hydrochloric acid and subsequent extraction using MTB ether. The combined organic phases are washed with water and sodium carbonate solution, and dried over sodium sulfate, and the solvent is distilled off.

Workup

  1. additionby adding
  2. extraction10 ml of 2 N hydrochloric acid and subsequent extraction
  3. washThe combined organic phases are washed with water and sodium carbonate solution
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-8c4fce8ae12640d4b37ed5170e644e90
Source dataset
uspto-grants-1999_07
Patent number
US05925767

Reaction notes

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