p-Toluenesulfonic acid → HCID 54144899, compound

HRID 264532Notes

Reaction equation

HRID 264532 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6]2.[CH3:13][CH:14](O)[CH:15]=[CH2:16].COC(OC)(C)C.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:13]([CH:7]1[CH2:6][C:5]2[C:9](=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:8]1=[O:12])[CH:14]=[CH:15][CH3:16]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 117163-Buten-2-olHCID 787875-Methoxyindan-1-one

Product 1

HCID 54144899HCID 54144899, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 50.0 g of 5-methoxy-1-indanone, 80 ml of 3-buten-2-ol, 132 ml of 2,2-dimethoxypropane and 600 mg of p-toluenesulfonic acid in 500 ml of toluene was brought to boiling. The resulting methanol/acetone mixture was distilled off and the reaction solution was subsequently boiled under reflux for an additional 48 hours. After cooling, the solution was evaporated in a vacuum. Purification on silica gel (hexane/diethyl ether 5:1) yielded 19.2 g (31%) of (RS)-2-(2-buten-1-yl)-5-methoxy-1-indanone as a pale yellow oil.

Workup

  1. distillationThe resulting methanol/acetone mixture was distilled off
  2. temperatureunder reflux for an additional 48 hours
  3. temperatureAfter cooling
  4. customthe solution was evaporated in a vacuum
  5. customPurification on silica gel (hexane/diethyl ether 5:1)

Sources & evidence

ORD record
ord-805641b429c242a5a30816f82fc220d4
Source dataset
uspto-grants-1997_07
Patent number
US05646173

Reaction notes

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