Hydrochloric Acid → Ethyl 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propylthio]-2-propylphenoxy]butyrate

HRID 704122Notes

Reaction equation

HRID 704122 reaction equation
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([SH:22])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].Br[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[C:30]([OH:37])[C:29]=1[CH2:38][CH2:39][CH3:40].[I-].[K+].C(=O)([O-])[O-].[K+].[K+].Cl>CC(C)=O>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:8]([CH2:19][CH2:20][CH3:21])[C:7]([S:22][CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([C:34](=[O:36])[CH3:35])=[C:30]([OH:37])[C:29]=2[CH2:38][CH2:39][CH3:40])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 15712395HCID 15712395, compound

Product 1

HCID 15712404Ethyl 4-[6-acetyl-3-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)-propylthio]-2-propylphenoxy]butyrateYield 71%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 4-(6-acetyl-3-mercapto-2-propylphenoxy)-butyrate (1.7 g), (4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl)-ethanone (1.7 g), potassium iodide (0.5 g) and potassium carbonate (1.45 g) in acetone (40 ml) was heated with refluxing and stirring for 7.5 hours. Ice-water and conc. hydrochloric acid were added thereto, and the mixture was subjected to extraction with ethyl acetate. After washed with water, the extract was dried over sodium sulfate and concentrated under a reduced pressure. The resultant residue was separated and purified through silica-gel column chromatography (eluting with benzene:ethyl acetate=9:1) to give the title compound (2.08 g, 71.0%) as light yellow crystal, mp 87-88° C.

Workup

  1. temperaturewas heated
  2. temperaturewith refluxing
  3. extractionthe mixture was subjected to extraction with ethyl acetate
  4. washAfter washed with water
  5. dry with materialthe extract was dried over sodium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe resultant residue was separated
  8. custompurified through silica-gel column chromatography (eluting with benzene:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-8ef416022a144fdc8d51a816f7678a61
Source dataset
uspto-grants-1991_01
Patent number
US04985585

Reaction notes

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