* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Regarding Example 2, instead of methanol, the same operation as in Example 2 was carried out except that ethanol was used. The residue was purified under reduced pressure distillation (boiling point: 110-119 ° C./1.5 Torr) to give 4-ethoxymethylphenol. Yield is 75percent. HPLC purity was 98percent. In a 200 mL three-necked flask equipped with thermometer, three way cock, stirrer, under a nitrogen stream, 15.0 g (0.12 mol) of 4-hydroxybenzyl alcohol, 69 g of methanol, 0.06 g of nitromethane were added. While stirring at room temperature, a mixed solution of 0.45 g of hydrochloric acid and 3.0 g of methanol was added dropwise, and the mixture was stirred at 35 ° C. for 3 hours. The area percentage of HPLC at the end of the reaction was 99percent. A mixed solution of 0.38 g of imidazole (manufactured by Aldrich Co., Ltd.) and 1.1 g of methanol was added dropwise to neutralize, and methanol was concentrated under reduced pressure. 60 g of isopropyl ether (manufactured by Nacalai Tesque, Inc.) and 22.5 g of water were added and extracted, and 27 g of water and 0.26 g of acetic acid (manufactured by Nacalai Tesque) were added to the organic layer and washed. After washing the organic layer twice with water, the organic layer was concentrated and seed crystals were added and the mixture was slowly cooled to about 8 ° C. The precipitated crystals were filtered and dried to obtain 12.0 g (yield: 72percent) of colorless 4-methoxymethylphenol. HPLC purity was 99percent.
Reference:
[1] Patent: JP5747348, 2015, B2, . Location in patent: Paragraph 0060; 0063-0065
[2] Recueil des Travaux Chimiques des Pays-Bas, 1955, vol. 74, p. 1448,1452
[3] Molecular Crystals and Liquid Crystals (1969-1991), 1985, vol. 130, p. 231 - 248
[4] Molecular crystals and liquid crystals, 1984, vol. 112, # 3-4, p. 319 - 324
2
[ 623-05-2 ]
[ 78-39-7 ]
[ 57726-26-8 ]
Reference:
[1] Bulletin de la Societe Chimique de France, 1988, # 5, p. 901 - 904
3
[ 95068-22-7 ]
[ 57726-26-8 ]
Reference:
[1] Bulletin of the Chemical Society of Japan, 1954, vol. 27, p. 53,58
With hydrogenchloride; In water; at 35.0℃; for 3.0h;
Regarding Example 2, instead of methanol, the same operation as in Example 2 was carried out except that ethanol was used. The residue was purified under reduced pressure distillation (boiling point: 110-119 C./1.5 Torr) to give 4-ethoxymethylphenol. Yield is 75%. HPLC purity was 98%.In a 200 mL three-necked flask equipped with thermometer, three way cock, stirrer, under a nitrogen stream, 15.0 g (0.12 mol) of 4-hydroxybenzyl alcohol, 69 g of methanol, 0.06 g of nitromethane were added. While stirring at room temperature, a mixed solution of 0.45 g of hydrochloric acid and 3.0 g of methanol was added dropwise, and the mixture was stirred at 35 C. for 3 hours. The area percentage of HPLC at the end of the reaction was 99%. A mixed solution of 0.38 g of imidazole (manufactured by Aldrich Co., Ltd.) and 1.1 g of methanol was added dropwise to neutralize, and methanol was concentrated under reduced pressure. 60 g of isopropyl ether (manufactured by Nacalai Tesque, Inc.) and 22.5 g of water were added and extracted, and 27 g of water and 0.26 g of acetic acid (manufactured by Nacalai Tesque) were added to the organic layer and washed. After washing the organic layer twice with water, the organic layer was concentrated and seed crystals were added and the mixture was slowly cooled to about 8 C. The precipitated crystals were filtered and dried to obtain 12.0 g (yield: 72%) of colorless 4-methoxymethylphenol. HPLC purity was 99%.