(2-HYDROXYMETHYL-4,5-DIIODO-PHENYL)-METHANOL synthesis
- Product Name:(2-HYDROXYMETHYL-4,5-DIIODO-PHENYL)-METHANOL
- CAS Number:53279-73-5
- Molecular formula:C8H8I2O2
- Molecular Weight:389.96
82679-28-5
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Yield:53279-73-5 91%
Reaction Conditions:
Stage #1: 4,5-diiodobenzene-1,2-dicarboxylic acidwith borane-THF in tetrahydrofuran at 0 - 66; for 42 h;Inert atmosphere;
Stage #2: with potassium carbonate in tetrahydrofuran;water at 50; for 12 h;Inert atmosphere;
Steps:
4.9. 4,5-Diiodobenzene-1,2-dimethanol (14)
In a 3-L three-necked flask were placed dry THF (1750 mL) and 13 (62.3 g, 149 mmol). A solution of 1M BH3 in THF (350 mL, 350 mmol) was added at 0 °C under Ar over 1 h. After the addition, the mixture was stirred at 0 °C for 1 h, and then refluxed at 66 °C for 40 h. After the mixture was cooled, saturated aqueous K2CO3 (1050 mL) was slowly added and stirring was continued for 12 h at 50 °C. The organic layer was separated and the aqueous layer was extracted with THF three times. The organic layers were combined and washed with saturated aqueous NaCl three times. The organic solvent was evaporated in vacuo. The solid was washed successively with hexane, dichloromethane, and water. The product was dried in vacuo to obtain 53.5 g, 91% of 14. White solid, mp: 163-165 °C. 1H NMR data matched published data.23 1H NMR (acetone-d6, 500 MHz): δ (ppm)=7.98 (s, 2H), 4.61 (d, 4H), 4.47 (t, 2H).
References:
Yamamoto, Koji;Takagi, Akuto;Hada, Miyako;Taniwaki, Ryosuke;Mizutani, Tadashi;Kimura, Yoshifumi;Takao, Yuko;Moriwaki, Kazuyuki;Matsumoto, Fukashi;Ito, Takatoshi;Iwai, Toshiyuki;Hida, Koichi;Mizuno, Takumi;Ohno, Toshinobu [Tetrahedron,2016,vol. 72,# 32,p. 4918 - 4924]
85-41-6
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68218-30-4
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632-80-4
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