Methanol → HCID 10080528, compound

Under nitrogen, into a quartz tube equipped with a dry-ice condenser was added anhydrous methanol (20 g, 0.62 mol) and di-tertiarybutylperoxide (.79 g, 0.003 mol). The quartz tube was placed in a Rayonet UV photochemical reactor and HFC 1234zc, CF3CH═CFH (5 g, 0.044 mol) was added drop-wise via a dry-ice condenser (−78° C.) over a period of ˜1 hour while being irradiated at (UV wavelength) 254 nm. After complete addition, the reaction mixture was irradiated for ˜1 hour. The reaction mixture was concentrated under reduced pressure. The residue was extracted in diethyl ether (˜50 mL), washed with 20 mL aq. Na2SO3 (20%) and brine (10 mL). The ether layer was then concentrated to afford 7 g of the crude material. Distillation of this material under reduced pressure (24-28 mm Hg) afforded CF3CH2CFHCH2OH (2.7g) as a colorless liquid; yield=42% based on HFC 1234 zc. Boiling point, 58° C./24 mm Hg. GC-MS: m/e at 146 (C4H6F4O) for M+; 19 F and 1H NMR spectra are consistent with the structure. 19 F NMR (CDCl3)δ=−64.6 (3F, m), −191.2 (1F, m) ppm; 1H NMR (CDCl3)δ=2.2 (1H, br), 2.4(1H, m), 2.6 (1H, m), 3.7-3.9 (2H, m), 4.9 (1H, dm) ppm.

1. customUnder nitrogen, into a quartz tube equipped with a dry-ice condenser
2. additionwas added drop-wise via a dry-ice condenser (−78° C.) over a period of ˜1 hour
3. customwhile being irradiated at (UV wavelength) 254 nm
4. additionAfter complete addition
5. customthe reaction mixture was irradiated for ˜1 hour
6. concentrationThe reaction mixture was concentrated under reduced pressure
7. extractionThe residue was extracted in diethyl ether (˜50 mL)
8. washwashed with 20 mL aq. Na2SO3 (20%) and brine (10 mL)
9. concentrationThe ether layer was then concentrated
10. customto afford 7 g of the crude material
11. distillationDistillation of this material under reduced pressure (24-28 mm Hg)

ORD record

ord-05d0f8c316b34f58a391a3d5612b42a1

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06673976B1