4-Toluenesulfonyl chloride → 2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl-p-toluenesulfonate

HRID 2308848Notes

Reaction equation

HRID 2308848 reaction equation
[OH-].[Na+].[CH2:3]1[C:13]2[CH2:12][CH2:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]([CH2:18][CH2:19][OH:20])[C:7]=2[CH2:6][CH:5]=[CH:4]1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([S:28](Cl)(=[O:30])=[O:29])=[CH:24][CH:23]=1>O.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH2:14]1[C:10]2[CH2:11][CH2:12][C:13]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=3[CH:8]([CH2:18][CH2:19][O:20][S:28]([C:25]3[CH:26]=[CH:27][C:22]([CH3:21])=[CH:23][CH:24]=3)(=[O:30])=[O:29])[C:9]=2[CH2:17][CH:16]=[CH:15]1

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 201879344,5,10,11-tetrahydro-1H-dibenzo[a,d]cycloheptene-5-ethanol

Product 1

HCID 867417722-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl-p-toluenesulfonate

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 664 g of sodium hydroxide in 996 ml of water is added to a solution, stirred at room temperature, of 87.5 g of crude 4,5,10,11-tetrahydro-1H-dibenzo[a,d]cycloheptene-5-ethanol, 103.7 g of p-toluenesulfochloride and 7.2 g of benzyltriethylammonium chloride in 1440 ml of methylene chloride and the mixture is stirred at room temperature overnight. The mixture is treated with 2 l of ice-water and extracted with 3 l of methylene chloride. The organic extracts are washed neutral with water. The aqueous extracts remaining are subsequently back-extracted three times with 2 l of methylene chloride each time. The organic extracts are combined, dried over magnesium sulfate and evaporated. After four-fold recrystallization of the solid residue from toluene, there is obtained pure 2-(4,5,10,11-tetrahydro-1H-dibenzo[a,d]cyclohepten-5-yl)ethyl-p-toluenesulfonate of melting point 150°-151°.

Workup

  1. extractionextracted with 3 l of methylene chloride
  2. washThe organic extracts are washed neutral with water
  3. extractionThe aqueous extracts remaining are subsequently back-extracted three times with 2 l of methylene chloride each time
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customAfter four-fold recrystallization of the solid residue from toluene

Sources & evidence

ORD record
ord-36a24758ee9f46ce85a9dac2bfa554da
Source dataset
uspto-grants-1987_09
Patent number
US04691040

Reaction notes

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