Triphenylmethanol is insoluble in water, but when it is treated with an acid, like concentrated sulfuric acid, it dissolves to create a bright yellow solution, due to the formation of a stable "trityl" carbocation. On dilution of the solution with more water, the color disappears, and triphenylmethanol precipitates from solution.
The presence of three adjacent phenyl groups confers special properties manifested in the reactivity of the alcohol. For example it reacts with acetyl chloride, not to give the ester, but triphenylmethyl chloride:[4]
Ph3COH + MeCOCl → Ph3CCl + MeCOOH
The three phenyl groups also offer steric protection. Reaction with hydrogen peroxide gives an unusually stable hydroperoxide, Ph3COOH.[5]
Triphenylmethanol forms 1:1 molecular complex with triphenylphosphine oxide.
Triphenylmethanol is sold by chemical suppliers.
Triphenylmethanol can be obtained from the Grignard reaction of phenylmagnesium bromide and methyl benzoate or benzophenone in diethyl ether.[7]
Another route involves reacting triphenylmethane with chromyl chloride in tetrachloromethane at 22 °C for 30 minutes. The yield is given as 99%.
Triphenylmethanol is insoluble in water, but when it is treated with concentrated sulfuric acid, a bright yellow solution results. As this yellow solution is diluted with water, its color disappears and a precipitate of triphenylmethanol reappears. Suggest a structure for the bright yellow species, and explain this unusual behavior.
Triphenylmethanol is an organic compound that is insoluble in water but soluble in alcohol and benzene. It appears as a yellow color due to the formation of stable trityl carbocation respectively.
Triphenylmethanol forms 1:1 molecular complex with triphenylphosphine oxide. It is a specific clathrate host for methanol and dimethyl sulphoxide and forms clathrate inclusion complexes. It undergoes reduction to triphenylmethane by 9, l0-dihydro-10-methylacridine in the presence of perchloric acid.
Triphenylmethanol is an aromatic organic compound. It is a white crystalline solid that is insoluble in water and petroleum ether, but well soluble in ethanol.
The triphenylmethanol derivatives are aromatic compounds, however in basic solutions, the aromaticity of phenolic rings is isolated. By decreasing the pH in acidic solutions, the hydroxy group of triphenylmethanol can absorb a proton and be eliminated from the molecule. The driving force for such a phenomenon is the chance of forming an integrated resonance system that is more stable. This phenomenon is responsible for changing the color in acidic and basic solutions. i.e. the isolated and integrated resonance systems absorb different wavelengths of light, therefore show different colors. Scheme 3 illustrates a mechanism of resonance structure conversion of triphenylmethanol derivatives 1a-k in basic and acidic solutions.