Ethanol → HCID 13338862, compound

HRID 652455Notes

Reaction equation

HRID 652455 reaction equation
[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#N)=[CH:15][C:14]=2[Cl:21])=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2].S(=O)(=O)(O)[OH:29].[CH2:33]([OH:35])[CH3:34]>>[C:1]([C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:35][CH2:33][CH3:34])=[O:29])=[CH:15][C:14]=2[Cl:21])=[C:6]([CH2:24][CH2:25][CH3:26])[C:5]=1[OH:27])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 13338859HCID 13338859, compound

Product 1

HCID 13338862HCID 13338862, compound

Procedure

A mixture of 1-(4-acetyl-3-hydroxy-2-n-propylphenoxy)-3-(2-chloro-4-cyanophenoxy)propane (1.86 g), ethanol (30 ml) and concentrated sulfuric acid (10 ml) was refluxed for 6 hours and then cooled to room temperature. The crystals were collected by filtration and dissolved in chloroform, the solution was washed with a saturated aqeuous sodium hydrogen carbonate solution and then with dilute hydrochloric acid and dried (sodium sulfate). Then, the chloroform was distilled off, and the residue was recrystallized from ethanol. There was obtained ethyl 4-[3-(4-acetyl-3-hydroxy-2-n-propylphenoxy)propoxy]-3-chlorobenzoate as colorless needles (1.1 g). Melting point 101°-102° C.

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationThe crystals were collected by filtration
  3. dissolutiondissolved in chloroform
  4. washthe solution was washed with a saturated aqeuous sodium hydrogen carbonate solution
  5. dry with materialwith dilute hydrochloric acid and dried (sodium sulfate)
  6. distillationThen, the chloroform was distilled off
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-da082f6de90c470aaf45252feabc5a53
Source dataset
uspto-grants-1987_06
Patent number
US04672073

Reaction notes

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