1-Bromohexane → HCID 20393997, compound

HRID 1862860Notes

Reaction equation

HRID 1862860 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1.[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.[I-].[K+]>[CH2:19]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:18])[C:7]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:8][O:9]2)=[CH:4][CH:3]=1)[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 81011-BromohexaneHCID 11430Potassium CarbonateHCID 53768917-Hydroxyisoflavone

Product 1

HCID 20393997HCID 20393997, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 4875Potassium IodideCatalystHCID 180AcetoneSolvent

Procedure

23.8 g of 7-hydroxy-isoflavone in 200 ml of anhydrous acetone are boiled, under stirring, with 18 g of n-hexyl bromide, 18 g of potassium carbonate and 1 g of potassium iodide for 72 hours under reflux condenser. The inorganic salts are removed by filtration, the filtrate is subjected to steam distillation in order to remove acetone and excess reagent, the precipitate is filtered and recrystallized from acetone, yielding 20 g of 7-n-hexyloxy-isoflavone, m.p. 120°-122° C. In a similar way, also 7-isopropyloxy-isoflavone, 7-n-butyloxy-isoflavone, and 7-n-amyloxy-isoflavone already characterized in Example 1, 7-isopropyloxy-2-methyl-isoflavone, 7-n-butyloxy-isoflavone and 7-n-amyloxy-isoflavone already characterized in Example 5, and

Workup

  1. temperatureunder reflux condenser
  2. customThe inorganic salts are removed by filtration
  3. distillationthe filtrate is subjected to steam distillation in order
  4. customto remove acetone and excess reagent
  5. filtrationthe precipitate is filtered
  6. customrecrystallized from acetone

Sources & evidence

ORD record
ord-78dba55b1f254bb8af20813eddf9213f
Source dataset
uspto-grants-1979_09
Patent number
US04166862

Reaction notes

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