Phenol → 1,3-Diphenoxy-2-propanol

Participants

Reaction Conditions

Reaction Steps

In a 100 mL pear-shaped flask were precisely weighed 0.579 g of tris[tris(dimethylamino)phosphoranylidene-amino]phosphine oxide ([(Me2N)3P=N]3P=O where Me is methyl, same in the following description) as a phosphine oxide represented by formula (1) which was substantially anhydrous by adequate drying over phosphorous pentoxide in a desiccator in vacuo (1.00 mmol) and 9.88 g of phenol (105 mmol). To the mixture warmed to 90° C. was added dropwise 15.0 g of phenyl glycidyl ether (referred to as "PGE"; same in the following description) (100 mmol) over 10 min. After addition, the mixture was stirred at the same temperature for 5 hours, and cooled to room temperature over about 10 min. A small portion of the reaction mixture was quantitatively analyzed by gas chromatography using 1,3,5-trichlorobenzene as an internal standard, indicating that the starting PGE had been almost completely consumed to form desired 1,3-diphenoxy-2-propanol in a yield of 96% based on PGE. In brief, the reaction almost quantitatively proceeded. The reaction mixture was directly subjected to column chromatography to give 22.5 g of 1,3-diphenoxy-2-propanol as a colorless solid in an isolation yield of 92% whose various analyses gave data identical to a reference standard. The catalyst activity (molar amount of a desired product per one mole of catalyst in a unit time; same in the following description) of tris[tris(dimethylamino)phosphoranylidene-amino]phosphine oxide was 20 mol/mol/h, which was surprisingly about 3, 2 or 1.5 times as large as that given by boron trifluoride, N-methylimidazole or triphenylphosphine in Comparative Example 2, 3 or 4, respectively.

Provenance & Evidence