Ethanol → HCID 13338862, compound

HRID 1285392Notes

Reaction equation

HRID 1285392 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-44a25baff19b42ce9c3ef0790a9e80a5
Source dataset
uspto-grants-1986_01
Patent number
US04567201

Reaction notes

Loading…