Water → 2-(2-Buten-1-yl)-8-chloro-1-tetralone

HRID 264545Notes

Reaction equation

HRID 264545 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[CH2:9][CH2:8][CH2:7]2.[CH3:13][CH:14](O)[CH:15]=[CH2:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>ClC(Cl)(Cl)Cl>[CH2:13]([CH:9]1[CH2:8][CH2:7][C:6]2[C:11](=[C:2]([Cl:1])[CH:3]=[CH:4][CH:5]=2)[C:10]1=[O:12])[CH:14]=[CH:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 117163-Buten-2-olHCID 113673658-Chloro-3,4-dihydro-2H-naphthalen-1-one

Product 1

HCID 543159702-(2-Buten-1-yl)-8-chloro-1-tetraloneYield 35%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

8.85 g of 8-chloro-1-tetralone were dissolved in 90 ml of tetrachloromethane under argon and added to 21.0 ml of 3-buten-2-ol and 190 mg of p-toluenesulfonic acid. The reaction solution was heated to reflux on a water separator for 9 days. The solvent was removed in a vacuum and the residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1 and then with hexane/ethyl acetate 4:1. In addition to large amounts of unreacted educt (8.3 g), there were obtained 4.1 g (35%) of 2-(2-buten-1-yl)-8-chloro-1-tetralone as a yellow oil.

Workup

  1. temperatureThe reaction solution was heated
  2. customThe solvent was removed in a vacuum
  3. customthe residue was chromatographed on 200 g of silica gel firstly with hexane/ethyl acetate 9:1
  4. additionIn addition to large amounts of unreacted educt (8.3 g)

Sources & evidence

ORD record
ord-f4ffefa9ea304c0b96d748a89f6c783f
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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