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

HRID 1288075Notes

Reaction equation

HRID 1288075 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-e45b5c5740264e4ab57e337f026041e3
Source dataset
uspto-grants-1976_10
Patent number
US03987079

Reaction notes

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