Sulfuric Acid → HCID 547246, compound

HRID 1730102Notes

Reaction equation

HRID 1730102 reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9]([CH3:17])(O)[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=2[CH2:6]1.S(=O)(=O)(O)O.[OH-].[K+]>C(Cl)Cl>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][CH:5]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[CH2:17])[C:8]2[CH:18]=[CH:19][CH:20]=[CH:21][C:7]=2[CH2:6]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14797Potassium HydroxideHCID 20359361HCID 20359361, compound

Product 1

HCID 547246HCID 547246, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8 g. (0.027 mole) of 10-(2-dimethylaminoethyl)-10,11-dihydro-5-methyl-5H-dibenzo[a,d]cyclohepten-5-ol and 250 ml. 2M-sulfuric acid is refluxed for 2 hours. The mixture is cooled in ice and made basic by the addition of solid potassium hydroxide. The mixture is extraced with methylene chloride. The methylene chloride is washed with water, dried over anhydrous magnesium sulfate and evapored in vacuo. The oily residue is distilled at 140° C/0.5 mm and the distillate is dissolved in ethanol. The resulting precipitate is filtered and recrystallized from diethylether-ethanol 1:1 to give the product 10-(2-dimethylaminoethyl)-10,11-dihydro-5-methylene-5H-dibenzo[a,d]cycloheptene, m.p. 171° to 172 C.

Workup

  1. additionA mixture of 8 g
  2. temperatureThe mixture is cooled in ice
  3. washThe methylene chloride is washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThe oily residue is distilled at 140° C/0.5 mm
  6. dissolutionthe distillate is dissolved in ethanol
  7. filtrationThe resulting precipitate is filtered
  8. customrecrystallized from diethylether-ethanol 1:1

Sources & evidence

ORD record
ord-7b84a6ed7d054ee7b26b42d11bf00432
Source dataset
uspto-grants-1976_11
Patent number
US03991102

Reaction notes

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