Acetic Acid → HCID 21275776, compound

HRID 231331Notes

Reaction equation

HRID 231331 reaction equation
[O:1]=[C:2]1[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]([O:20][Si:21]([CH2:26][CH3:27])([CH2:24][CH3:25])[CH2:22][CH3:23])([C:16]([F:19])([F:18])[F:17])[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C(O)(=O)C.O>C(O)C.[Zn]>[OH:1][CH:2]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=2[C:9]([O:20][Si:21]([CH2:24][CH3:25])([CH2:26][CH3:27])[CH2:22][CH3:23])([C:16]([F:18])([F:19])[F:17])[C:10]2[C:15]1=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 14343500HCID 14343500, compound

Product 1

HCID 21275776HCID 21275776, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 50 mg (0.13 mmol) of 9,10-dihydro-9-oxo-10-triethylsiloxy-10-trifluoromethylanthracen in 0.5 mL of absolute ethanol was treated successively with 42 mg (0.65 mmol) of zinc dust and 0.5 mL of a solution of 90% acetic acid - 20% water. The mixture was heated to reflux in a 110° C. oil bath for 2 hours, allowed to cool to room temperature, and poured into 10 mL of water. The resulting aqueous mixture was extracted with three 5 mL portions of diethyl ether. Combination, drying, and concentration of the ether layers gave a residue which was purified by PTLC (one 1 mm silica gel plate eluted with 50% dichloromethane - 50% petroleum ether) to give 34 mg of 87% pure (58% yield) 9,10-dihydro-9-hydroxy-10-triethysiloxy-10-trifluoromethylanthracene as a white solid: mass spectrum (70 eV) m/z (relative intensity) 363 (8, M-C2H5), 211 (100), 183 (21), 77 (25); TMS derivative 466(M+), 368 (27), 246 (24), 196 (22), 193 (90), 165 (21), 105 (40), 87 (28), 77 (47), 73 (100), 59 (20), 45 (21).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto cool to room temperature
  3. extractionThe resulting aqueous mixture was extracted with three 5 mL portions of diethyl ether
  4. customCombination, drying
  5. customconcentration of the ether layers gave a residue which
  6. customwas purified by PTLC (one 1 mm silica gel plate eluted with 50% dichloromethane - 50% petroleum ether)

Sources & evidence

ORD record
ord-911df782d4934018a94c3c1985da4070
Source dataset
uspto-grants-1989_07
Patent number
US04845258

Reaction notes

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