Toluene → HCID 13384229, compound

HRID 2419910Notes

Reaction equation

HRID 2419910 reaction equation
[OH:1][C:2]([C:12]([F:15])([F:14])[F:13])([C:8]([F:11])([F:10])[F:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[C:18]1(C)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[O:1]([C:2]([C:8]([F:11])([F:10])[F:9])([C:12]([F:13])([F:14])[F:15])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 3

HCID 1140TolueneHCID 24758Sodium hydrideHCID 13384220HCID 13384220, compound

Product 1

HCID 13384229HCID 13384229, compound

Procedure

Ethyl 2-hydroxy-3,3,3-trifluoro-2-trifluoromethylpropionate (12.0 g.) is added, dropwise at 0° C. under nitrogen, to a stirred mixture of toluene (200 ml.) and sodium hydride (2.0 g. of a 60% dispersion in oil from which the oil has been washed with toluene). The mixture is stirred at ambient temperature for 1.5 hours, and phenyl-2-thienyliodonium trifluoroacetate (20.0 g.) is added. The mixture is heated under reflux with continued stirring for 1 hour, then cooled, and filtered. The filtrate is evaporated in vacuo, and the residual red oil (22.2 g.) is fractionally distilled at 24 mm. pressure to give ethyl 2-phenoxy-3,3,3-trifluoro-2-trifluoromethylpropionate, b.p. 103°-105° C. (9.4 g.).

Workup

  1. washof a 60% dispersion in oil from which the oil has been washed with toluene)
  2. additionphenyl-2-thienyliodonium trifluoroacetate (20.0 g.) is added
  3. temperatureThe mixture is heated
  4. temperatureunder reflux
  5. stirringwith continued stirring for 1 hour
  6. temperaturecooled
  7. filtrationfiltered
  8. customThe filtrate is evaporated in vacuo
  9. distillationthe residual red oil (22.2 g.) is fractionally distilled at 24 mm

Sources & evidence

ORD record
ord-67cbfb055abb4b4b8e64f3247bf1836d
Source dataset
uspto-grants-1978_08
Patent number
US04107329

Reaction notes

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