Brey, Mary L.’s team published research in Journal of the American Chemical Society in 79 | CAS: 2358-54-5

Journal of the American Chemical Society published new progress about 2358-54-5. 2358-54-5 belongs to ethers-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol,Ether, name is 2-(2,2,2-Trifluoroethoxy)ethanol, and the molecular formula is C4H7F3O2, SDS of cas: 2358-54-5.

Brey, Mary L. published the artcilePreparation and properties of some vinyl and glycidyl fluoro ethers, SDS of cas: 2358-54-5, the publication is Journal of the American Chemical Society (1957), 6533-6, database is CAplus.

KOH (94 g.) in 500 cc. (CH2OH)2 in an autoclave chilled with Dry Ice-Me2CO, treated with approx. 2.5 moles of the appropriate 1,1-difluoronolefin, rocked at room temperature overnight, poured into iced H2O, and the organic layer washed, dried, and distilled yielded the corresponding glycol monoether; in this manner were prepared the following ROCH2CH2OH (R, % yield, b.p./mm., n25D, d25, and MRD given): CHClFCF2, 54, 114-18°/100, 1.3795/21°, -, -; CHCl2CF2 (I), 30, 62-3°/2, 1.4245, 1.4905, 33.42; CF3CHFCF2, 25, 72-4°/40, 1.3192, 1.5227, 27.57. As a by-product of I was also obtained 18% (CHCl2CH2OCH2)2, b2.2 90°, n25D5 1.4194, d25 1.5786, MRD 52.50, hydrolyzed with concentrated H2SO4 to 31% (CHCl2CO2CH2)2, b3 148-50°, n25D 1.4840, d25 1.5386, MRD 52.79. KOH (5.0 g.) in 1.5 moles of the appropriate fluoro alc. treated in an autoclave at -78° with 44 g. ethylene oxide, rocked 4 hrs. at 70°, and worked up gave the corresponding glycol monoether; in this manner were prepared the following ROCH2CH2OH (same data as above given): CF3CH2, 50, 84°/80, 1.3502, 1.2902, 24.04; C2F5CH2, 32, 87°/84, 1.3370, 1.3806, 29.24; C3F7CH2, 62, 91-2°/54, 1.3300/28°, 1.4965/28°, 33.90; CF3CMe2, 35, 92°/77, 1.3749/22°, 1.1931/22°, 33.02. The appropriate fluoroalkyl hydroxyethyl ether (about 0.25 mole) treated with stirring with 60 g. PCl5 in portions, refluxed 20 min., cooled, poured into iced H2O, washed, dried, and fractionated yielded the corresponding compounds RO(CH2)2Cl (II) consistently in 27% yield; when the reaction mixture was diluted with about 100 cc. CHCl3 the yields were 45-67%. In this manner were prepared the following II (same data given): CHClFCF2 (III), 27, 85°/100, 1.3882, 1.4471, -; CHCl2CF2 (IV), 27, 86-7°/33, 1.4270, 1.4833, 36.95; CF3CHFCF2, 27, 46°/37, 1.3349, 1.4749, 32.33; CF3CH2, 53, 114-15°/760, 1.3590/27°, 1.3034/27°, 27.46; C3F7CH2, 67, 75°/80, 1.3381, 1.4673, 37.32; CF3CMe2, 45, 135°/760, 1.3784, 1.2102, 36.34; C2F5CH2, 49, 120-1°/760, 1.3448/26°, 1.3792/26°, 32.72. Hydrolysis of III yielded 34% CH2ClCH2O2CHClF, b47 106°, b45 105°, n23D 1.4369, d25 1.4256, MRD 32.20; IV gave similarly 36% CHCl2CO2(CH2)2Cl, b760 207-11°, n25D 1.4716, d25 1.4544, MRD 36.85. The appropriate II (0.20 mole) treated dropwise with stirring and heating with 18 g. KOH in 120 cc. PrOH, the distillate poured into H2O, and the organic layer washed, dried, and distilled yielded the corresponding compounds ROCH:CH2 (same data given): CHClFCF2, 52, 71-3°/760, 1.3531, 1.2408, -; CF3CH2, 32, 42-8°/760, 1.3180/27°, 1.118/ 27°, -; C2F5CH2, 21, 54-60°/760, 1.3131/27°, 1.227/27°, 27.92; C3F7CH2, 18, 78-82°/760, 1.3118/26°, 1.343/26°, 31.08. The appropriate fluoro alc. (0.50 mole) and 46 g. epichlorohydrin added to 25 g. NaOH in 300 cc. cold H2O kept at room temperature overnight, and the organic layer worked up gave mixtures of the epoxy ether and the diether. CF3CH2OH gave in this manner 31% CF3CH2OCH2CH.CH2.O, b760 132-5°, n25D 1.3560, d25 1.2666, MRD 26.93, and 19% (CF3CH2OCH2)2CHOH, b16 86°, n25D 1.3528, d25 1.3890, MRD 39.97. C2F5CH2OH gave similarly 19% C2F5CH2OCH2CH.CH2.O, b86-84 81-79°, n25D 1.3419, d25 1.3534, MRD 32.08. C3F7CH2OH gave 23% C3F7CH2OCH2CH.CH2.O, b49 79°, n25D 1.3350, d25 1.4429, and 24% (C3F7CH2OCH2)2CHOH, b15 112-15°, n25D 1.3338, d25 1.5569, MRD 60.40. CF3CH2OH (100 g.), 185 g. epichlorohydrin, and 2 cc. pyridine heated 12 hrs. with stirring at 80-90° gave 50% CF3CH2OCH2CH(OH)CH2Cl, b19 85-6°, n25D 1.3951, d25 1.3716, MRD 1.3716.

Journal of the American Chemical Society published new progress about 2358-54-5. 2358-54-5 belongs to ethers-buliding-blocks, auxiliary class Trifluoromethyl,Fluoride,Aliphatic hydrocarbon chain,Alcohol,Ether, name is 2-(2,2,2-Trifluoroethoxy)ethanol, and the molecular formula is C4H7F3O2, SDS of cas: 2358-54-5.

Referemce:
https://en.wikipedia.org/wiki/Ether,
Ether | (C2H5)2O – PubChem