Sulfuric Acid → 1-[(2,2-Dichloroethenyl)oxy]-3-methylbenzene

HRID 372470Notes

Reaction equation

HRID 372470 reaction equation
C(O[CH:5]([O:10][C:11]1[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=1)[C:6](Cl)([Cl:8])[Cl:7])(=O)C.S(=O)(=O)(O)O.[OH-].[Na+]>CO>[Cl:7][C:6]([Cl:8])=[CH:5][O:10][C:11]1[CH:12]=[C:13]([CH3:17])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 205689273-(2,2,2-Trichloro-1-acetoxy-ethoxy)-toluene

Product 1

HCID 205689261-[(2,2-Dichloroethenyl)oxy]-3-methylbenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
15 °C

Procedure

By an electrochemical reductive dehydrohalogenation method. 1(3-tolyloxy)-2,2,2-trichloroethyl acetate (15.8 g), concentrated sulphuric acid (98% w/v, 9.8 g) and methanol (220 ml) was charged into an electrolytic cell, which was surrounded by a cooling bath set to maintain the temperature at about 15° C, and fitted with a cylindrical diaphragm, stirrer, reference electrode (SCE) and a working electrode. The cathode was a lead plate (surface area about 40 cm2). Using a current density in the range 5 to 10 mA/cm2 the reaction was conducted in the potential range -1100 to 1700 mV (SCE). When reduction was completed the cathodic electrolyte was neutralised with caustic soda and extracted with methylene chloride, the extracts dried over anhydrous sodium sulphate and evaporated to yield a residue of crude 3-tolyl 2,2-dichlorovinyl ether.

Workup

  1. customwas surrounded by a cooling bath
  2. customfitted with a cylindrical diaphragm, stirrer, reference electrode (SCE)
  3. extractionextracted with methylene chloride
  4. dry with materialthe extracts dried over anhydrous sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-77d7be18253d4d49a373caa8ec5609b6
Source dataset
uspto-grants-1978_05
Patent number
US04091110

Reaction notes

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