3-(Trifluoromethyl)phenol → HCID 21079531, compound

HRID 1375229Notes

Reaction equation

HRID 1375229 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)([F:4])([F:3])[F:2].[CH2:12]([CH:14]1[O:16][CH2:15]1)[Cl:13].C([O-])([O-])=O.[K+].[K+]>>[Cl:13][CH2:12][CH:14]([OH:16])[CH2:15][O:11][C:7]1[CH:8]=[CH:9][CH:10]=[C:5]([C:1]([F:3])([F:2])[F:4])[CH:6]=1

Participants

4

Reactant 3

HCID 73763-(Trifluoromethyl)phenolHCID 7835EpichlorohydrinHCID 11430Potassium Carbonate

Product 1

HCID 21079531HCID 21079531, compoundYield 99.8%

Conditions

Temperature
70 °C

Procedure

A mixture of m-CF3C6H4OH (48.6 g, 0.30 mol), epichlorohydrin (138.8 g, 1.50 mol) and K2CO3 (20.7 g, 0.15 mol) was stirred at 70° C. for 2 h. Epichlorohydrin was evaporated in vacuo. Water (250 mL) was added and the resulting mixture was extracted with CH2Cl2 (2×50 mL). The combined organic extract was stirred with 32% HCl (50 mL) for 0.5 h at rt. The organic layer separated, dried over Na2SO4, filtered and concentrated in vacuo to give 76.2 g of crude 1-chloro-3-[3-(trifluoromethyl)phenoxy]-2-propanol which was used in next step without additional treatment.

Workup

  1. customEpichlorohydrin was evaporated in vacuo
  2. additionWater (250 mL) was added
  3. extractionthe resulting mixture was extracted with CH2Cl2 (2×50 mL)
  4. extractionThe combined organic extract
  5. stirringwas stirred with 32% HCl (50 mL) for 0.5 h at rt
  6. customThe organic layer separated
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1117a2863758460c86c31324d8ad5046
Source dataset
uspto-grants-2007_01
Patent number
US07166730B2

Reaction notes

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