P-Xylene → 2-(2,5-Dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

HRID 1873934Notes

Reaction equation

HRID 1873934 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[F:9][C:10]([F:18])([F:17])[C:11]([C:13]([F:16])([F:15])[F:14])=[O:12]>[Cl-].[Al+3].[Cl-].[Cl-].Cl>[F:9][C:10]([F:18])([F:17])[C:11]([C:3]1[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=1[CH3:1])([OH:12])[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 2

HCID 7809P-XyleneHCID 12695Hexafluoroacetone

Product 1

HCID 27750852-(2,5-Dimethylphenyl)-1,1,1,3,3,3-hexafluoropropan-2-olYield 88.2%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A 1 L reactor was charged under nitrogen with 200.0 g (1.88 mol) of p-xylene and 12.5 g (0.094 mol/0.05 eq) of aluminum chloride, followed by adjusting the inside temperature to 18° C. Then, 327.7 g (1.97 mol/1.05 eq) of hexafluoroacetone was introduced in a temperature range of 18-25° C. After the introduction, stirring was conducted at room temperature for 3 hr. Then, 200 mL of 10% hydrochloric acid was added. The resulting aqueous layer was extracted two times with 50 mL of chloroform. The resulting organic layers were combined together, followed by removing water with anhydrous magnesium sulfate, filtration, concentration, and vacuum distillation, thereby obtaining 451.3 g of 2-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-1,4-dimethylbenzene represented by the following formula. Upon this, purity was 92%, and yield was 81%.

Workup

  1. customto 18° C
  2. extractionThe resulting aqueous layer was extracted two times with 50 mL of chloroform
  3. customby removing water
  4. filtrationwith anhydrous magnesium sulfate, filtration, concentration, and vacuum distillation

Sources & evidence

ORD record
ord-a3ab1ddc8b754a9bb07f48c596c41347
Source dataset
uspto-grants-2012_11
Patent number
US08304508B2

Reaction notes

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