Potassium Iodide → Ethyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-6-(4-benzylphenyl)hexanoate

HRID 543215Notes

Reaction equation

HRID 543215 reaction equation
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([CH:14](Br)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][CH2:26][CH2:27][C:28]1[C:33]([OH:34])=[C:32]([C:35]([CH3:37])=[O:36])[CH:31]=[CH:30][C:29]=1[OH:38].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[C:35]([C:32]1[CH:31]=[CH:30][C:29]([O:38][CH:14]([C:11]2[CH:12]=[CH:13][C:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:9][CH:10]=2)[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:28]([CH2:27][CH2:26][CH3:25])[C:33]=1[OH:34])(=[O:36])[CH3:37]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27751982',4'-Dihydroxy-3'-propylacetophenoneHCID 13881964Ethyl 6-(4-benzylphenyl)-6-bromo-hexanoate

Product 1

HCID 13881965Ethyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-6-(4-benzylphenyl)hexanoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 9.75 g. of ethyl 6-(4-benzylphenyl)-6-bromo-hexanoate, 5.03 g. of 2,4-dihydroxy-3-propylacetophenone, 3.57 g. of potassium carbonate, and 1.0 g. of potassium iodide in 175 ml. of acetone was heated to reflux for about 86 hours. The reaction was evaporated in vacuo and the residue was purified by chromatography over silica gel eluting with a 0-20% ethyl acetate gradient in hexane. The appropriate fractions were pooled and evaporated, giving 2.5 g. of the desired product which was used for the subsequent hydrolysis. NMR was consistent with the compound ethyl 6-(4-acetyl-3-hydroxy-2-propylphenoxy)-6-(4-benzylphenyl)hexanoate.

Workup

  1. temperatureto reflux for about 86 hours
  2. customThe reaction was evaporated in vacuo
  3. customthe residue was purified by chromatography over silica gel eluting with a 0-20% ethyl acetate gradient in hexane
  4. customevaporated
  5. customgiving 2.5 g

Sources & evidence

ORD record
ord-3e9ae09b22e64a9bbd7d94a775108cd0
Source dataset
uspto-grants-1987_04
Patent number
US04661505

Reaction notes

Loading…