1,3-Benzenedimethanol, 5-(1,1-dimethylethyl)-2-hydroxy- synthesis
- Product Name:1,3-Benzenedimethanol, 5-(1,1-dimethylethyl)-2-hydroxy-
- CAS Number:2203-14-7
- Molecular formula:C12H18O3
- Molecular Weight:210.27
Yield:2203-14-7 97%
Reaction Conditions:
Stage #1: para-tert-butylphenolwith sodium hydroxide in water at 50;
Stage #2: formaldehyd in water at 20; for 72 h;
Steps:
3.2.1 2.3.2.1. Synthesis of (5-(tert-butyl)-2-hydroxy-1,3-phenylene)dimethanol
2.3.2.1
Synthesis of (5-(tert-butyl)-2-hydroxy-1,3-phenylene)dimethanol
4-(tert-butyl)phenol (20 mmol, 3.0 g) was added to an aqueous 4% NaOH solution (24 mL) and the mixture stirred at 50 °C to dissolve the starting material.
After cooling to room temperature, 37% HCHO solution (5.5 mL) was added and the obtained mixture was stirred for 3 days.
Then concentrated HCl (2.5 mL) was added to quench the reaction.
The mixture was extracted with chloroform, and the extract was washed with water and brine.
The organic layer was dried over anhydrous MgSO4.
The solvent was evaporated in vacuo and the residue was purified by column chromatography on 230-400 mesh of silica gel (petroleum ether/ethyl acetate = 5/3) to afford (5-(tert-butyl)-2-hydroxy-1,3-phenylene)dimethanol as a colorless oil in 97% yield (4.08 g).
1H NMR (400 MHz, CDCl3) δ (ppm) 1.27 (singlet, 9H), 2.52 (broad, 2 H), 4.80 (singlet, 4H), 7.08 (singlet, 2H), 7.90 (broad, 1H).
References:
Yu, Shasha;Wang, Yishan;Ma, Yujie;Wang, Limin;Zhu, Jia;Liu, Shenggao [Inorganica Chimica Acta,2017,vol. 468,p. 159 - 170]
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