Aluminum → HCID 67945072, compound

HRID 1382007Notes

Reaction equation

HRID 1382007 reaction equation
[Al].[C:2]([C:6]1[C:7](=[O:28])[C:8](C(C)(C)C)=[CH:9][C:10](O[Si](CC)(CC)CC)([C:12]([F:15])([F:14])[F:13])[CH:11]=1)([CH3:5])([CH3:4])[CH3:3]>O>[C:2]([C:7]1([OH:28])[C:6]([C:2]([CH3:4])([CH3:5])[CH3:3])=[CH:11][C:10]([C:12]([F:14])([F:13])[F:15])=[CH:9][CH2:8]1)([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 5359268AluminumHCID 14343497HCID 14343497, compound

Product 1

HCID 67945072HCID 67945072, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
70 °C

Procedure

A strip of aluminum foil weighing 264 mg (9.8 mmol) was amalgamated by immersion in a solution of 2% mercuric chloride in water for 15 seconds, washed with absolute ehtanol followed by diethyl ether, cut into small pieces, and added to a solution of 412 mg of 96% pure (0.98 mmol) 2,6-di-tert-butyl-4-triethylsiloxy-4-trifluoromethyl-2,5-cyclohexadien-1-one in 25 mL of 10% water - 90% tetrahydrofuran. The resulting mixture was heated at 70° C. for 1.5 hours, allowed to cool to room temperature, and filtered. The filter cake was washed with tetrahydrofuran. Concentration of the combined filtrates gave a residue which was poured into 25 mL of water. The aqueous mixture was extracted with three 10 mL portions of dichloromethane. Combination, drying (MgSO4), and concentration of the organic layers gave a residue which was purified by PTLC (one 2 mm silica gel plate eluted with petroleum ether), affording 247 mg of 95% pure (87% yield) 1,6-di-tert-butyl-4-trifluoromethylphenol. An analytical sample was obtained by crystallization from methanol: mp 78°-80° C.; 1H NMR (CDCl3)δ1.45 (s, 18H), 5.56 (broad s, 1H), 7.50 (s, 1H); 19F NMR (CDCl3, relative to CFCl3)-61.7 ppm (s); IR (KBr) 3632, 2963, 1337, 1319, 1241, 1167, 1141, 1109, 893, 668 cm-1 ; mass spectrum (70 eV) m/z (relative intensity) 274 (20, M+), 259 (100), 231 (28), 57 (57), 41 (54). Anal. Calcd. for C15H21F3O: C, 65.67; H, 7.72. Found: C, 65.46; H, 7.94.

Workup

  1. washwashed with absolute ehtanol
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. washThe filter cake was washed with tetrahydrofuran
  5. customConcentration of the combined filtrates gave a residue which
  6. extractionThe aqueous mixture was extracted with three 10 mL portions of dichloromethane
  7. dry with materialCombination, drying (MgSO4), and concentration of the organic layers
  8. customgave a residue which
  9. customwas purified by PTLC (one 2 mm silica gel plate eluted with petroleum ether)

Sources & evidence

ORD record
ord-f768e3ee75e24d3896fa01d01bf1ea0d
Source dataset
uspto-grants-1989_02
Patent number
US04804773

Reaction notes

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