Trifluoroacetic acid → (2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methane

HRID 1111283Notes

Reaction equation

HRID 1111283 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=1[OH:21])O.C([SiH](CC)CC)C.FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH2:11][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[C:14]=1[OH:21]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 22151942(2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methanol

Product 1

HCID 22151955(2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methaneYield 130.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

(2-Methoxymethoxyphenyl)(2-hydroxy-3-methoxyphenyl)methanol (15.54 g, 54 mmol) and triethylsilane (7.53 g, 0.064 mol) were dissolved in 150 ml of methylene chloride and the solution cooled to 0° C. and blanketed with nitrogen. A solution of 7.39 g (64.8 mmol) of trifluoroacetic acid in 70 ml of methylene chloride was added with stirring and cooling and the mixture was allowed to react for 2 hours. The reaction mixture was then poured into saturated aqueous sodium bicarbonate, more methylene chloride added, and the organic layer recovered. This was extracted with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over magnesium sulfate, and concentrated by evaporation under reduced pressure to obtain 19.34 g of orange oil. This was purified by preparative liquid chromatography eluting with a 5:95 mixture of acetone and hexane to obtain 3.95 g (27 percent of theory) of the title compound as an oil. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. temperaturecooling
  2. customto react for 2 hours
  3. additionadded
  4. customthe organic layer recovered
  5. extractionThis was extracted with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-fcbd055e473d4e0486d947b556a8dff6
Source dataset
uspto-grants-1990_12
Patent number
US04979978

Reaction notes

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