p-Toluenesulfonic acid → HCID 59608924, compound

HRID 1047477Notes

Reaction equation

HRID 1047477 reaction equation
[Br:1][CH2:2][CH2:3][C:4]1[C:12]([CH3:13])=[C:11]([CH3:14])[CH:10]=[C:9]2[C:5]=1[CH2:6][CH:7]([CH3:17])[CH:8]2OC.CC1C=CC(S(O)(=O)=O)=CC=1.BrCCC1C(C)=C(C)C=C2C=1C=C(C)C2>C1(C)C=CC=CC=1>[Br:1][CH2:2][CH2:3][C:4]1[C:12]([CH3:13])=[C:11]([CH3:14])[CH:10]=[C:9]2[C:5]=1[CH2:6][C:7]([CH3:17])=[CH:8]2

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 59608871HCID 59608871, compoundHCID 68740994HCID 68740994, compound

Product 1

HCID 59608924HCID 59608924, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a hot (110° C.) solution of 6.28 g (21.13 mmol) of 4-(2-bromoethyl)-1-methoxy-2,5,6-trimethylindane in 75 ml of toluene 0.4 g of TsOH*H2O was added. This mixture was refluxed with Dean-Stark trap for 10 min and then passed through the layer of Silica Gel 60 (40-63 um, d 80 mm, l 50 mm). The Silica Gel layer was additionally washed by 300 ml of toluene. The combined organic extract was evaporated to dryness. The product was isolated by flash chromatography using a short column with Silica Gel 60 (40-63 um, d 80 mm, l 50 mm; eluent: hexanes). Yield 5.38 g (96%) of 4-(2-bromoethyl)-2,5,6-trimethyl-1H-indene.

Workup

  1. temperatureThis mixture was refluxed with Dean-Stark trap for 10 min
  2. washThe Silica Gel layer was additionally washed by 300 ml of toluene
  3. extractionThe combined organic extract
  4. customwas evaporated to dryness
  5. customThe product was isolated by flash chromatography

Sources & evidence

ORD record
ord-13d1ca53d0224456a1698d1951dcc6cc
Source dataset
uspto-grants-2013_10
Patent number
US08569532B2

Reaction notes

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