Hydrochloric Acid → HCID 12898548, compound

HRID 2050070Notes

Reaction equation

HRID 2050070 reaction equation
[F:1][C:2]([F:19])([F:18])[C:3]([C:9]1[CH:15]=[C:14]([CH3:16])[C:12](N)=[C:11]([CH3:17])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5].Cl.N([O-])=O.[Na+].C(OC([S-])=[S:29])C.[K+]>O>[F:1][C:2]([F:19])([F:18])[C:3]([C:9]1[CH:15]=[C:14]([CH3:16])[C:12]([SH:29])=[C:11]([CH3:17])[CH:10]=1)([OH:8])[C:4]([F:7])([F:6])[F:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12753462-(4-Amino-3,5-dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-olHCID 2735045Potassium ethylxanthateHCID 23668193Sodium Nitrite

Product 1

HCID 12898548HCID 12898548, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To 4-(hexafluoro-2-hydroxy-2-propyl)-2,6-dimethylaniline (20 g=70 mmol), add 50 ml 4 N HCl. Reflux 1 hr., cool to 0° C., and add over 1 hour NaNO2 (6.0 g=87 mmol) in 13 ml H2O. After 30 min., add to 45° C. solution of potassium ethylxanthate (14.3 g=83 mmol) in 40 ml H2O. Keep at 45° C. for 30 minutes, cook, and extract with ether. Dry and concentrate. Dissolve the oil in 100 ml EtOH, add potassium hydroxide (17.5 g) and reflux 1 hour. Concentrate, than add 50 ml water and 10 ml concentrated sulfuric acid. Add 0.5 g zinc dust and steam distill. Extract the distillate with ether, dry and concentrate. Recrystallize from hexane to obtain 4-(hexafluoro-2-hydroxy-2-propyl)-2,6-dimethylthiophenol, m.p. 62°-64° C.

Workup

  1. temperatureReflux 1 hr
  2. waitKeep at 45° C. for 30 minutes
  3. extractionextract with ether
  4. customDry
  5. concentrationconcentrate
  6. dissolutionDissolve the oil in 100 ml EtOH
  7. additionadd potassium hydroxide (17.5 g)
  8. temperaturereflux 1 hour
  9. concentrationConcentrate
  10. additionthan add 50 ml water and 10 ml concentrated sulfuric acid
  11. additionAdd 0.5 g zinc dust and steam
  12. distillationdistill
  13. extractionExtract the distillate with ether
  14. customdry
  15. concentrationconcentrate
  16. customRecrystallize from hexane

Sources & evidence

ORD record
ord-cc1e30bc01a747e492abc92addbd82f0
Source dataset
uspto-grants-1980_04
Patent number
US04199597

Reaction notes

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