Potassium Iodide → 3,5-Heptanedione, 4-[6-(4-hydroxyphenyl)hexyl]-

HRID 426879Notes

Reaction equation

HRID 426879 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]Br)=[CH:4][CH:3]=1.COC1C=CC(CCCCCCBr)=CC=1.B(Br)(Br)Br.[I-].[K+].[CH3:36][CH2:37][C:38](=[O:44])[CH2:39][C:40](=[O:43])[CH2:41][CH3:42].C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl.CC(C)=O>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:39]([C:38](=[O:44])[CH2:37][CH3:36])[C:40](=[O:43])[CH2:41][CH3:42])=[CH:4][CH:3]=1

Participants

9

Reactant 6

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 819233,5-HeptanedioneHCID 10588171Benzene, 1-(6-bromohexyl)-4-methoxy-HCID 106587816-(4-Hydroxyphenyl)hexyl bromide

Product 1

HCID 5143233,5-Heptanedione, 4-[6-(4-hydroxyphenyl)hexyl]-

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 0.5 mole of 6-(4-hydroxyphenyl)hexyl bromide [pepared from 6-(4-methoxyphenyl)hexyl bromide and boron tribromide in methylene dichloride according to the procedure of Example 42f], 0.125 mole of potassium iodide, 1.15 moles of 3,5-heptanedione and 1.05 moles of powdered anhydrous potassium carbonate (dried in vacuo for two hours) in 2 liters of acetone is stirred at reflux for 24 hours. One liter of solvent is distilled off and the remainder of the reaction mixture is poured with stirring into a solution of 4 liters of ice-water containing 160 ml. of concentrated hydrochloric acid. The separated product is extracted with ether and the ether extracts washed with saturated sodium chloride solution and dried over anhydrous magnesium sulfate. The ether is distilled off in vacuo and the excess 3,5-heptanedione removed at 70° C. (0.8 mm.) in a rotary evaporator. The residual product is crystallized from isopropyl alcohol-pentane to give 4-[6-(4-hydroxyphenyl)hexyl]-3,5-heptanedione.

Workup

  1. temperatureat reflux for 24 hours
  2. distillationOne liter of solvent is distilled off
  3. additionthe remainder of the reaction mixture is poured
  4. stirringwith stirring into a solution of 4 liters of ice-water containing 160 ml
  5. extractionThe separated product is extracted with ether
  6. washthe ether extracts washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe ether is distilled off in vacuo
  9. customthe excess 3,5-heptanedione removed at 70° C. (0.8 mm.)
  10. customin a rotary evaporator
  11. customThe residual product is crystallized from isopropyl alcohol-pentane

Sources & evidence

ORD record
ord-9c258a9e4ca64734afcddc9ecafcaeb5
Source dataset
uspto-grants-1979_10
Patent number
US04171378

Reaction notes

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