HCID 21425449, compound → HCID 21425443, compound

HRID 258993Notes

Reaction equation

HRID 258993 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([O:8][C:9]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:10]=2[C:11]([OH:13])=O)[CH:5]=[CH:6][CH:7]=1>S(=O)(=O)(O)O>[F:19][C:18]([F:20])([F:21])[C:15]1[CH:16]=[CH:17][C:9]2[O:8][C:4]3[C:5](=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)[C:11](=[O:13])[C:10]=2[CH:14]=1

Participants

3

Reactant 1

HCID 21425449HCID 21425449, compound

Product 1

HCID 21425443HCID 21425443, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

700 grams of 2-(3-fluorophenyloxy)-5-trifluormethylbenzoic acid were dissolved in 3000 milliliters of concentrated sulfuric acid whereby the temperature rose to 60° C. The mixture was stirred at 45°-50° C for one hour and then poured onto 10 liters of crushed ice. The precipitate was filtered off, suspended in 1000 milliliters of acetone, made alkaline with concentrated aqueous ammonia and reprecipitated with ice and water to a volume of 10 liters. The precipitate was filtered, washed with water and dried in vacuum; whereupon it was recrystallized to yield 167 grams of 2-trifluoromethyl-6-fluoroxanthen-9-one which melts at 140°-142° C.

Workup

  1. customrose to 60° C
  2. filtrationThe precipitate was filtered off
  3. customreprecipitated with ice and water to a volume of 10 liters
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried in vacuum
  7. customwhereupon it was recrystallized

Sources & evidence

ORD record
ord-b69064e865dd4b1c816c5477163109fb
Source dataset
uspto-grants-1977_07
Patent number
US04035503

Reaction notes

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