Methanol → 1,3-Benzenediol, 4,4′-[(2-hydroxy-5-methyl-1,3-phenylene)bis(methylene)]bis-

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Reaction Conditions

Reaction Steps

To a 5 L 3-necked flask equipped with a reflux condenser was added 2.1 L of methanol, 754 g of resorcinol, 215 g of 2,6-bis(hydroxymethyl)-p-cresol and 4.38 g of p-toluenesulfonic acid monohydrate. The solution was then heated to and kept at reflux for 20 hours. A distillation head was added to the flask and 1.1 L of methanol removed by distillation over a one hour period. The reaction mixture was then slowly added over a 30 minute period using an addition funnel into 20 L of de-mineralized water. The precipitate was slurried for one hour and then collected using a Buchner funnel. The crude product was added to 6 L de-mineralized water, heated to 85-87° C. and slurried for 20 minutes at this temperature. The suspension was vacuum filtered while at 85° C. and the filtrate allowed to cool to ambient temperature overnight. The filtrant was again extracted with 3.0 L of de-mineralized water for 20 minutes at 85° C., the mixture was vacuum filtered and cooled. The precipitates from the filtrates were collected on a Buchner and vacuum oven dried at 100° C. A combined yield of 158 g was obtained having a purity of about 91 % as determined by HPLC analysis.

Provenance & Evidence