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3,5-bis(hydroxylmethyl)benzoic acid synthesis

5synthesis methods
methyl 3,5-bis(hydroxymethyl)benzoate

193953-02-5
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3,5-bis(hydroxylmethyl)benzoic acid

123065-60-1
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Yield:123065-60-1 98%

Reaction Conditions:

with sodium hydroxide in methanol;water monomer at 25; for 16 h;

Steps:

Compound13-3

To a solution of compound13-2(175 mg, 0.892 mmol) inMeOH(2 mL) was added 2 mL sodium hydroxide aqueous solution (70 mg, 1.75 mmol) andthe resulting mixturestirred at room temperature for 16 hrs beforeadjusted pH to 3 with 1MHCl.The reaction mixturewas extracted with dichloromethane (3 × 10 mL). The organic phase was combined and dried over anhydrous Na2SO4, filtered and evaporated to dryness in vacuo, afforded compound13-3(159 mg, 98.0% yield)as a whitesolid.1H NMR (400 MHz, DMSO-d6) δ 12.85 (s, 1H), 7.77 (s, 2H), 7.48 (s, 1H), 5.30 (t,J= 5.6Hz, 2H), 4.60 (m, 4H).

References:

Bian, Hongzhu;Dong, Xun;Fu, Rong;Li, Congcong;Liu, Chang;Shen, Zhengwu;Xu, Wei;Xu, Zhenye;Zhang, Jinghua;Zhao, Xiaozhen;Zou, Xiaosu [European Journal of Medicinal Chemistry,2021,vol. 225,art. no. 113754] Location in patent:supporting information