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

HRID 839176Notes

Reaction equation

HRID 839176 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 (Example 28), 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-d3680836ed314e42b2181c3137bf2c32
Source dataset
uspto-grants-1978_06
Patent number
US04093736

Reaction notes

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