Potassium Iodide → 4-[10-(4-Carbethoxyphenoxy)decyl]-3,5-heptanedione

HRID 2163418Notes

Reaction equation

HRID 2163418 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C:13](=[O:16])[CH2:14][CH3:15])[C:9](=[O:12])[CH2:10][CH3:11].[OH:17][C:18]1[CH:28]=[CH:27][C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[C:22]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH2:2][CH2:3][CH2:4][CH2:5][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([C:13](=[O:16])[CH2:14][CH3:15])[C:9](=[O:12])[CH2:10][CH3:11])=[CH:28][CH:27]=1)([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 123634064-(6-Bromohexyl)heptane-3,5-dione

Product 1

HCID 227536734-[10-(4-Carbethoxyphenoxy)decyl]-3,5-heptanedione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 26.3 g. (0.0758 mole) of 4-(6-bromohexyl)-3,5-heptanedione, 13.1 g. (0.0787 mole) of ethyl p-hydroxybenzoate, 31.5 g. (0.228 mole) of powdered potassium carbonate, 4 g. of potassium iodide and 500 ml. of acetone was heated at reflux for 36 hours. The reaction mixture was concentrated in vacuo and partitioned between water and methylene dichloride. The organic layer was washed successively with sodium hydroxide solution, water, hydrochloric acid, water and sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solution was concentrated and the residue crystallized and recrystallized from n-pentane to give 4-[10-(4-carbethoxyphenoxy)decyl]-3,5-heptanedione, m.p. 45°-46° C.

Workup

  1. additionA mixture of 26.3 g
  2. temperatureat reflux for 36 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompartitioned between water and methylene dichloride
  5. washThe organic layer was washed successively with sodium hydroxide solution, water, hydrochloric acid, water and sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated
  8. customthe residue crystallized
  9. customrecrystallized from n-pentane

Sources & evidence

ORD record
ord-552d12a6d45e432cb6749a14c8e198ac
Source dataset
uspto-grants-1979_01
Patent number
US04133959

Reaction notes

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