Hydrochloric Acid → HCID 131713970, compound

HRID 1980112Notes

Reaction equation

HRID 1980112 reaction equation
[OH:1][CH:2]([C:7](=[O:25])[C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:16]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:18]=[CH:19][CH:20]=2)=[CH:10][CH:9]=1)S(O)(=O)=O.[Na].Cl.S(=O)=O>O>[OH2:1].[O:25]=[C:7]([C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=2)=[CH:10][CH:9]=1)[CH:2]=[O:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 5360545SodiumHCID 13376810HCID 13376810, compound

Product 1

HCID 131713970HCID 131713970, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 374 g. portion of hydroxy[p-(α,α,α-trifluoro-m-tolyloxy)benzoyl]methanesulfonic acid, sodium salt was suspended in 3485 ml. of water and the mixture was stirred at 50° C. while 316 ml. of 6N hydrochloric acid were added during 30 minutes. The cloudy solution was warmed slowly until sulfur dioxide evolution ceased and an oil began to separate at about 75° C., then was stirred and heated at reflux for 1.5 hours. The mixture was cooled and extracted with three 1000 ml. portions of ether. The extracts were combined, washed with water, saturated sodium bicarbonate and brine, dried and concentrated to a yellow solid. This solid was recrystallized from ether:hexane (1:1) at 5° C., to yield the desired product as a white solid, m.p. 73°-80° C.

Workup

  1. customto separate at about 75° C.
  2. temperatureheated
  3. temperatureat reflux for 1.5 hours
  4. temperatureThe mixture was cooled
  5. extractionextracted with three 1000 ml
  6. washwashed with water, saturated sodium bicarbonate and brine
  7. customdried
  8. concentrationconcentrated to a yellow solid
  9. customThis solid was recrystallized from ether:hexane (1:1) at 5° C.

Sources & evidence

ORD record
ord-2c4f6fc54e1c4f7c81aebcf44989d388
Source dataset
uspto-grants-1984_11
Patent number
US04485114

Reaction notes

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