Aluminum → HCID 14343509, compound

HRID 1382020Notes

Reaction equation

HRID 1382020 reaction equation
[Al].[O:2]=[C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6](O[Si](CC)(CC)CC)([C:13]([F:16])([F:15])[F:14])[CH:5]=[CH:4]1>O>[F:14][C:13]([F:15])([F:16])[C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]([OH:2])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 5359268AluminumHCID 14343499HCID 14343499, compound

Product 1

HCID 14343509HCID 14343509, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
70 °C

Procedure

A strip of aluminum foil weighing 278 mg (10 mmol) was amalgamated by immersion in a solution of 2% mercuric chloride in water for 15 seconds, washed with absolute ethanol followed by diethyl ether, cut into small pieces, and added to a solution of 353 mg (1.0 mmol) of 1,4-dihydro-1-oxo-4-triethylsiloxy-4-trifluoromethylnaphthalene in 10 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 diethyl ether. 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 dichloromethane), affording 190 mg (90% yield) of 4-trifluoromethyl-1-naphthol as a white solid. An analytical sample was obtained by recrystallization from dichloromethane-hexane: mp 132°-133° C.; 1H NMR (CDCl3) δ5.50 (broad s, 1H), 6.79 (d, 1H, J=8 Hz), 7.50-7.80 (m, 3H), 8.10-8.45 (m, 2H); 19F NMR (CDCl3, relative to CFCl3) -59.5 ppm (s); IR (KBr) 3327, 1580, 1385, 1355, 1327, 1260, 1251, 1241, 1195, 1178, 1146, 1120, 1111, 1101, 1056, 767, cm-1 ; mass spectrum (70 eV) m/z (relative intensity) 212 (100, M+), 133 (32), 115 (100). Anal. Calcd. for C11H7F3O: C, 62.27; H, 3.33. Found: C, 61.82; H, 3.50.

Workup

  1. washwashed with absolute ethanol
  2. temperatureto cool to room temperature
  3. filtrationfiltered
  4. washThe filter cake was washed with diethyl ether
  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 dichloromethane)

Sources & evidence

ORD record
ord-7e857206eb3442e7b2861e9048f9e18a
Source dataset
uspto-grants-1989_02
Patent number
US04804774

Reaction notes

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