Sulfuric Acid → Ethane, 2-chloro-1,1-bis(p-methoxyphenyl)-

HRID 1449289Notes

Reaction equation

HRID 1449289 reaction equation
[Cl:1][CH:2]=[C:3](Cl)Cl.[C:6]1([O:12][CH3:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.S(=O)(=O)(O)O>C(O)(=O)C>[CH3:13][O:12][C:6]1[CH:11]=[CH:10][C:9]([CH:3]([C:9]2[CH:10]=[CH:11][C:6]([O:12][CH3:13])=[CH:7][CH:8]=2)[CH2:2][Cl:1])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6575TrichloroethyleneHCID 7519Anisole

Product 1

HCID 3014331Ethane, 2-chloro-1,1-bis(p-methoxyphenyl)-

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
15 °C

Procedure

To a 500-milliliter jacketed flask equipped with a mechanical stirrer, thermometer, and dropping funnel, and cooled to approximately 2° C. with circulating trichloroethylene thermostated cooling liquid, was charged 43.2 grams (0.40 mole) of anisole and 30.6 grams (0.20 mole) of commercial chloroacetal. To the cooled and stirred solution was added a solution of 80.0 grams (0.82 mole) of concentrated sulfuric acid dissolved in 50 milliliters of glacial acetic acid over a 1.17-hour period (1 hour and 10 minutes) at a rate sufficient to maintain the temperature at less than 15° C. When the addition was complete, the solution was stirred an additional 10 minutes, allowed to warm to 15° C. and poured into 1 liter of an ice/water mixture. The mixture was extracted with three 150-milliliter portions of diethyl ether, washed successively with three 100-milliliter portions of saturated aqueous sodium carbonate and three 100-milliliter portions of cold water, and dried over anhydrous sodium sulfate. Evaporation of the ether in vacuo yielded 55.0 grams (almost quantitative) of crude 1,1-bis(4-methoxyphenyl)-2-chloroethane as a colorless oil.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureTo the cooled
  3. temperatureto maintain the temperature at less than 15° C
  4. additionWhen the addition
  5. stirringthe solution was stirred an additional 10 minutes
  6. extractionThe mixture was extracted with three 150-milliliter portions of diethyl ether
  7. washwashed successively with three 100-milliliter portions of saturated aqueous sodium carbonate and three 100-milliliter portions of cold water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customEvaporation of the ether in vacuo

Sources & evidence

ORD record
ord-4c805749c19748209221bf6c284c48bf
Source dataset
uspto-grants-1980_02
Patent number
US04189610

Reaction notes

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