Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → HCID 818594, compound

HRID 127909

Reaction equation

HRID 127909 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9](=[O:15])[CH2:8][CH2:7][CH2:6][C:5]2=1.[Cl:16][CH2:17][CH2:18]OS(C1C=CC(C)=CC=1)(=O)=O.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:18][CH2:17][Cl:16])[C:10]1[C:9](=[O:15])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

6

Reactant 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 14798Sodium HydroxideHCID 6079846-methyl-2,3,4,9-tetrahydro-1H-carbazol-1-one

Product 1

HCID 818594HCID 818594, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Procedure

100 g. (0.5 mole) of 6-methyl-1,2,3,4-tetrahydrocarbazol-1-one and 234.5 g. (1 mole) of p-toluenesulfonic acid-β-chloroethylester are dissolved in 700 ml. of toluene and stirred together with a solution of 4.25 g. (12.5 m moles) of tetrabutylammoniumhydrogensulfate in 500 ml. of aqueous sodium hydroxide solution (30% strength) for 10 hours at room temperature. The organic layer is separated, washed with water and concentrated by evaporation. 108 g. (=83% of the theoretical) of 6-methyl-9-(2-chloroethyl)-1,2,3,4-tetrahydrocarbazol-1-one (melting at 106° to 107° C.) are thus obtained.

Workup

  1. customThe organic layer is separated
  2. washwashed with water
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-739c9d0811b2474db0f52f67dad9d8eb
Source dataset
uspto-grants-1981_03
Patent number
US04258043

Linked notes

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