Toluene → 2,2,2-Trifluoroethanol

HRID 36466

Reaction equation

HRID 36466 reaction equation
[CH2:1]([Al:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH2:8]([OH:13])[C:9]([F:12])([F:11])[F:10].C1(C)C=CC=CC=1>>[F:10][C:9]([F:12])([F:11])[CH2:8][O-:13].[Al+3:3].[F:10][C:9]([F:12])([F:11])[CH2:8][O-:13].[F:10][C:9]([F:12])([F:11])[CH2:8][O-:13].[Al:3]([CH2:6][CH3:7])([CH2:4][CH3:5])[CH2:1][CH3:2].[CH2:8]([OH:13])[C:9]([F:12])([F:11])[F:10]

Participants

6

Reactant 3

HCID 1140TolueneHCID 64092,2,2-TrifluoroethanolHCID 16682930Triethylaluminum

Product 3

HCID 64092,2,2-TrifluoroethanolHCID 16682930TriethylaluminumHCID 19419412Aluminum trifluoroethoxide

Conditions

Temperature
-25 °C

Procedure

Aluminum trifluoroethoxide was prepared by treatment of a toluene solution of triethylaluminum (0.38M) with these equivalents of trifluoroethanol at -25° C. After gas evolution was complete, the reaction mixture was allowed to stand at room temperature. When precipitation of product appeared to be well-advanced (1-2 hr), the reaction mixture was cooled at -25° C. for 18 hr before collecting the solid product. From 1.76 mmol of Et3Al and 0.528 g trifluoroethanol was obtained 435 mg of white solid, mp 171°-172° C. 1H NMR (THF-d8): 4.1 (q, J=8). 19F NMR (THF-d8): -77.0 (bd s), trace signals at -76.3 and-77.7.

Workup

  1. customto stand at room temperature
  2. customWhen precipitation of product
  3. custom(1-2 hr)
  4. custombefore collecting the solid product

Sources & evidence

ORD record
ord-6733c848ab3a417fbc7b41988b3b42bc
Source dataset
uspto-grants-1995_05
Patent number
US05414140

Linked notes

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