M-Xylene → HCID 57557802, compound

HRID 1873933Notes

Reaction equation

HRID 1873933 reaction equation
[C:1]1([CH3:8])[CH:6]=[CH:5][CH:4]=[C:3]([CH3:7])[CH:2]=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:6]1[CH:5]=[CH:4][C:3]([CH3:7])=[CH:2][C:1]=1[CH3:8])([OH:12])[C:13]([F:16])([F:15])[F:14]

Participants

5

Reactant 2

HCID 7929M-XyleneHCID 12695Hexafluoroacetone

Product 1

HCID 57557802HCID 57557802, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 6451240Aluminum(III) ChlorideCatalystHCID 313Hydrochloric AcidSolvent

Procedure

A 1 L reactor was charged under nitrogen with 100.0 g (0.94 mol) of m-xylene and 6.3 g (0.047 mol/0.05 eq) of aluminum chloride, followed by adjusting the inside temperature to 10° C. Then, 164.2 g (0.99 mol/1.05 eq) of hexafluoroacetone was introduced in a temperature range of 10-25° C. After the introduction, stirring was conducted at room temperature for 1 hr. Then, 100 mL of 10% hydrochloric acid was added. The resulting aqueous layer was extracted two times with 40 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 227.6 g of 4-[2,2,2-trifluoro-1-hydroxy-1-(trifluoromethyl)ethyl]-1,3-dimethylbenzene represented by the following formula. Upon this, purity was 95%, and yield was 84%.

Workup

  1. customto 10° C
  2. extractionThe resulting aqueous layer was extracted two times with 40 mL of chloroform
  3. customby removing water
  4. filtrationwith anhydrous magnesium sulfate, filtration, concentration, and vacuum distillation

Sources & evidence

ORD record
ord-0ae185e172734e31bea1387fd3bb2222
Source dataset
uspto-grants-2012_11
Patent number
US08304508B2

Reaction notes

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