Potassium Iodide → 4-{6-[4-(2-Ethoxyethoxy)phenyl]hexyl}-3,5-heptanedione

HRID 1449224Notes

Reaction equation

HRID 1449224 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][CH:14]([C:19](=[O:22])[CH2:20][CH3:21])[C:15](=[O:18])[CH2:16][CH3:17])=[CH:4][CH:3]=1.[CH2:23]([O:25][CH2:26][CH2:27]Br)[CH3:24].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:23]([O:25][CH2:26][CH2:27][O:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH:14]([C:15](=[O:18])[CH2:16][CH3:17])[C:19](=[O:22])[CH2:20][CH3:21])=[CH:6][CH:7]=1)[CH3:24]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 611412-Bromoethyl ethyl etherHCID 5143233,5-Heptanedione, 4-[6-(4-hydroxyphenyl)hexyl]-

Product 1

HCID 234557264-{6-[4-(2-Ethoxyethoxy)phenyl]hexyl}-3,5-heptanedione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3.9 g. of 4-[6-(4-hydroxyphenyl)hexyl]3,5-heptanedione, 12 g. of 2-bromoethyl ethyl ether, 4 g. of potassium carbonate and 1 g. of potassium iodide in 40 ml. of acetone was heated at reflux for 48 hours and then allowed to stand at room temperature for three days. The reaction mixture was then filtered and concentrated to remove the solvent. The residue was distilled at 200°-205° C. (0.001 mm.) to give 4-{6-[4-(2-ethoxyethoxy)phenyl]hexyl}-3,5-heptanedione as a light yellow oil.

Workup

  1. additionA mixture of 3.9 g
  2. temperatureat reflux for 48 hours
  3. filtrationThe reaction mixture was then filtered
  4. concentrationconcentrated
  5. customto remove the solvent
  6. distillationThe residue was distilled at 200°-205° C. (0.001 mm.)

Sources & evidence

ORD record
ord-c815ab35df444917a347a233af9895f5
Source dataset
uspto-grants-1980_02
Patent number
US04189500

Reaction notes

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