[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([CH3:9])=[CH:4][C:3]=1[OH:10].[OH-:11].[Na+].O.[CH2:14]=O.[C:16](O)(=[O:18])C>>[OH:11][CH2:1][C:2]1[C:7]([CH3:8])=[C:6]([CH2:16][OH:18])[C:5]([CH3:9])=[C:4]([CH3:14])[C:3]=1[OH:10]Into a 2 liter four-necked flask were charged 136.19 g of 2,3,5-trimethylphenol, 48.0 g of sodium hydroxide and 480 g of water. While stirring at 40° C., 486.91 g of 37% formaldehyde was added dropwise thereto over one hour, and the reaction was conducted for 3 more hours. After completion of the reaction, 180.15 g of 90% aqueous acetic acid solution was added for neutralization, then the mixture was cooled to25° C. and filtered. The filtrate was extracted with 1000 g of ethylacetate and the ethyl acetate layer was washed with water and concentrated.To the concentrated mass, 500 g of toluene was added and the mixture was cooled to 20° C. and filtered. The filter cake thus obtained was rinsed with 400 g of toluene and dried a whole day and night at 45°C. under reduced pressure to obtain 100 g of 2,4-bis(hydroxymethyl)-3,5,6-trimethylphenol.
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