p-Toluenesulfonic acid → HCID 54126438, compound

HRID 365972Notes

Reaction equation

HRID 365972 reaction equation
[Cl:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[OH:11].[CH:12]([O:14][CH2:15][CH3:16])=[CH2:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>ClC1C=CC=CC=1>[Cl:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 8023Ethyl vinyl etherHCID 6994770HCID 6994770, compound

Product 1

HCID 54126438HCID 54126438, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A stirrer, thermometer and reflux condenser were mounted to a 100-ml three-necked flask which was filled with 10.0 g (0.059 mol) of trans-2-chloroindan-1-ol, 13 ml of monochlorobenzene and 4.72 g (0.066 mol) of ethyl vinyl ether. While the mixture was stirred, 5.6 g (0.03 mol) of p-toluenesulfonic acid was added and stirred for 3 hours at 25° C. to form trans-2-chloro-1-(1-ethoxyethoxy)indane in the reaction system. Moreover, to the reaction liquid was added 123.4 g (0.77 mol) of a 25% aqueous solution of NaOH and 1.44 g (0.0035 mol) of tetrabutylammonium bromide and the mixture was stirred for 30 hours at 103° C. to form 1-(1-ethoxyethoxy)indene in the reaction system. The reaction liquid was separated into a monochlorobenzene layer and a water layer. To the monochlorobenzene layer were added 20 ml of water and 0.65 g (0.0065 mol) of 98% sulfuric acid and the mixture was stirred for 1 hour at 78° C. After the reaction, the reaction liquid was separated into a monochlorobenzene layer and a water layer, and the monochlorobenzene layer was rinsed twice with 100 ml of water. The monochlorobenzene layer was dried with anhydrous sodium sulfate and then vacuum-concentrated to obtain 6.93 g of a black oil of 1-indanone (giving a yield of 88.4%). The purity of this oil according to gas chromatography (GC) was 63.9% (surface area percentage). The IR spectrum of this oil matches the IR spectrum of commercial 1-indanone.

Workup

  1. temperatureA stirrer, thermometer and reflux condenser
  2. customwere mounted to a 100-ml three-necked flask
  3. stirringstirred for 3 hours at 25° C.

Sources & evidence

ORD record
ord-4be2b55ed1034cce8a0cdbf9af2557d5
Source dataset
uspto-grants-2000_10
Patent number
US06127579

Reaction notes

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