Methanol → HCID 12531836, compound

HRID 1704034Notes

Reaction equation

HRID 1704034 reaction equation
Cl(O)(=O)(=O)=O.[OH2:6].[OH2:7].O.[N+]([O-])([O-])=O.[Tl+].[F:14][C:15]([F:33])([F:32])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([C:29](=O)[CH3:30])=[CH:25][CH:24]=2)[CH:17]=1.[CH3:34]O>>[F:14][C:15]([F:33])([F:32])[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][C:23]2[CH:28]=[CH:27][C:26]([CH2:29][C:30]([O:7][CH3:34])=[O:6])=[CH:25][CH:24]=2)[CH:17]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 24247Perchloric AcidHCID 125318311-{4-[3-(Trifluoromethyl)phenoxy]phenyl}ethan-1-oneHCID 18700168HCID 18700168, compound

Product 1

HCID 12531836HCID 12531836, compound

Procedure

A solution of 73.5 ml of 70% perchloric acid in 370 ml of methanol is cooled to 0° C and 73.76 g of thallium nitrate trihydrate followed by 42.25 g of 4'-(α,α,α-trifluoro-m-tolyloxy)acetophenone are added. The mixture is allowed to stir overnight while warming to room temperature. A white solid is rmoved by filtration and the filtrate is diluted with one liter of water. The resulting mixture is extracted with three 200 ml portions of chloroform. The combined organic extracts are washed with two 200 ml portions of water, 200 ml of saturated NaHCO3, saturated NaCl and dried over MgSO4. Evaporation of the solvent affords a yellow oil, which is filtered through aluminum oxide (benzene) and distilled at 0.07 mm to give the product as a yellow oil, bp 120°-148° C.

Workup

  1. additionare added
  2. filtrationA white solid is rmoved by filtration
  3. additionthe filtrate is diluted with one liter of water
  4. extractionThe resulting mixture is extracted with three 200 ml portions of chloroform
  5. washThe combined organic extracts are washed with two 200 ml portions of water, 200 ml of saturated NaHCO3, saturated NaCl
  6. dry with materialdried over MgSO4
  7. customEvaporation of the solvent
  8. customaffords a yellow oil, which
  9. filtrationis filtered through aluminum oxide (benzene)
  10. distillationdistilled at 0.07 mm

Sources & evidence

ORD record
ord-0f262ce447f140a18a70c91de156b6cb
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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