Indene → 1H-Indene, 3-(3-bromopropyl)-

HRID 427108Notes

Reaction equation

HRID 427108 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Br:10][CH2:11][CH2:12][CH2:13]Br>[OH-].[Na+]>[Br:10][CH2:11][CH2:12][CH2:13][C:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]=1

Participants

4

Reactant 2

HCID 7219IndeneHCID 80011,3-Dibromopropane

Product 1

HCID 105378211H-Indene, 3-(3-bromopropyl)-

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

The compound is prepared as described by Makoska in Tetrahedron Letters 38, 4621-4624 (1966) by adding a mixture of 580 g (5 M) indene and 1010 g (5 M) 1,3-dibromopropane to 1500 ml 50% aqueous NaOH containing 50 ml 40% methanolic Triton B. The temperature is held below 55° C. by cooling in an ice bath. After stirring 6 hours the reaction mixture is diluted to 4 l. The layers are separated and the aqueous layer is extracted two times with ether. The combined organic layers are extracted two times with water, dried over MgSO4, filtered and the solvent is removed. The oily product is distilled and redistilled at reduced pressure collecting 432 g (36.6%) boiling 126°-140°/0.1 mm.

Workup

  1. customThe compound is prepared
  2. additionby adding
  3. customis held below 55° C.
  4. temperatureby cooling in an ice bath
  5. additionis diluted to 4 l
  6. customThe layers are separated
  7. extractionthe aqueous layer is extracted two times with ether
  8. extractionThe combined organic layers are extracted two times with water
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customthe solvent is removed
  12. distillationThe oily product is distilled
  13. distillationredistilled at reduced pressure
  14. customcollecting 432 g (36.6%)
  15. customboiling 126°-140°

Sources & evidence

ORD record
ord-022a7bc170d248a3b9ca04470769056d
Source dataset
uspto-grants-1979_10
Patent number
US04172945

Reaction notes

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