Hydrochloric Acid → Ethyl 8-methyl-2,3-dihydrobenz-1,4-oxathiin-7-carboxylate

HRID 849450Notes

Reaction equation

HRID 849450 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].Cl.CCOCC>[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 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 at room temperature for 45 min. Working-up is carried out by addition of 10 ml of 2N hydrochloric acid and subsequent extraction with MTB ether. The combined organic phases are washed with water and sodium carbonate solution, dried over sodium sulfate and the solvent is distilled off.

Workup

  1. washThe combined organic phases are washed with water and sodium carbonate solution
  2. dry with materialdried over sodium sulfate
  3. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-055dc7eb6f4941eab96d358c45e5d903
Source dataset
uspto-grants-2000_01
Patent number
US06013607

Reaction notes

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