Hydrogen Bromide → HCID 5323829, compound

HRID 1732857Notes

Reaction equation

HRID 1732857 reaction equation
[CH3:1][C:2]1[CH2:9][CH2:8][CH:7]=[C:6]([CH3:10])[CH2:5][CH2:4][CH:3]=1.CC1CCC(C)=CCCC=1.[BrH:21]>>[CH3:10][C:6]12[CH:3]([Br:21])[C:2]([CH3:1])([CH2:4][CH2:5]1)[CH2:9][CH2:8][CH2:7]2

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 773703760-13-2HCID 773711,5-Dimethylcycloocta-1,5-diene

Product 1

HCID 5323829HCID 5323829, compoundYield 93.3%

Procedure

A mixture of 68 g (0.5 mol) 1,5-dimethyl-1,5-cyclooctadiene and 1,6-dimethyl-1,5-cyclooctadiene (ratio 80/20) was boiled under stirring for 1 hour with 500 ml 48% hydrogen bromide and 10 g of AMBERLYST A15 ion-exchange resin. Thereafter, the reaction product was subjected to azeotrope distillation with the aqueous hydrogen bromide solution. The distillate was then extracted with pentane. The pentane layer was treated as described in Example 1a. By fractional distillation under reduced pressure 81 g 1,5-dimethyl-8-bromobicyclo[3,2,1]octane (b.p. 93° C./10 mm Hg) was obtained in 93.3% yield. The purity of the product according to gas-liquid chromatography was more than 98%.

Workup

  1. distillationdistillation with the aqueous hydrogen bromide solution
  2. extractionThe distillate was then extracted with pentane
  3. additionThe pentane layer was treated
  4. distillationBy fractional distillation under reduced pressure 81 g 1,5-dimethyl-8-bromobicyclo[3,2,1]octane (b.p. 93° C./10 mm Hg)
  5. customwas obtained in 93.3% yield

Sources & evidence

ORD record
ord-b8268b6022a4445b8676f5c63c05a9d1
Source dataset
uspto-grants-1980_12
Patent number
US04239707

Reaction notes

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