9,10-dimethylphenanthrene-9,10-diol synthesis
- Product Name:9,10-dimethylphenanthrene-9,10-diol
- CAS Number:7251-51-6
- Molecular formula:C16H16O2
- Molecular Weight:0
Yield:7251-51-6 77.02%
Reaction Conditions:
in tetrahydrofuran; for 2 h;
Steps:
Synthesis of 9,10-Dimethyl-9,10-dihydrophenanthrene-9,10-diol (2).
A solution of compound 1 (2 g, 9.61 mmol) in 120 mL of THF was added into a 250 mL one-necked flask.A methylmagnesium chloride solution in THF (3 M; 8.34 mL, 24.01 mmol) was added drop-wise into the flask for 10 min. The reaction mixture was stirred for 2 h and then quenched with 0.25 M aqueous HCl. The reaction mixture was thrice extracted with acetic ether. The combined extracts were dried with anhydrous magnesium sulfate and concentrated using a rotary evaporator. The crude product was purified by column chromatography using ethyl acetate/hexane (v/v = 1:4) as the eluent. The yield of the resulting white solid (2) was 77.02 % (1.78 g). 1H NMR (300 MHz, acetone-d6) δ 7.80 (m, 4H), 7.38 (m, 4H), 3.65 (s, 2H), 1.35(s, 6H).
References:
Mi, Dongbo;Park, Jong Baek;Xu, Fei;Kim, Hee Un;Kim, Ji-Hoon;Hwang, Do-Hoon [Bulletin of the Korean Chemical Society,2014,vol. 35,# 6,p. 1647 - 1653]
