Methanol → 2,2,4,4,4-Pentafluorobutan-1-ol

Under nitrogen, into a quartz reactor equipped with a dry-ice condenser was added anhydrous methanol (100 g, 3.10 mol) and di-tertiarybutylperoxide (3.95 g, 0.015 mol). The quartz reactor tube was placed in a Rayonet UV photochemical reactor and HFC 1225, CF3CH═CF2 (57.9 g, 0.438 mol) was added drop-wise via a dry-ice condenser (−78° C.) over a period of ˜5 hours while being irradiated at 254 nm. After complete addition, the reaction mixture was irradiated for additional hour. Then the reaction mixture was concentrated under reduced pressure, the residue (˜65 g) was mixed well with 120 mL aq. Na2SO3 (20%), separated the lower layer, and washed with brine (40 mL). The crude product was then distilled under reduced pressure (24-28 mm Hg) to afford 55 g CF3CH2CF2CH2OH (yield 77% based on HFC 1225).

1. customUnder nitrogen, into a quartz reactor equipped with a dry-ice condenser
2. additionwas added drop-wise via a dry-ice condenser (−78° C.) over a period of ˜5 hours
3. customwhile being irradiated at 254 nm
4. additionAfter complete addition
5. customthe reaction mixture was irradiated for additional hour
6. concentrationThen the reaction mixture was concentrated under reduced pressure
7. additionthe residue (˜65 g) was mixed well with 120 mL aq. Na2SO3 (20%)
8. customseparated the lower layer
9. washwashed with brine (40 mL)
10. distillationThe crude product was then distilled under reduced pressure (24-28 mm Hg)

ORD record

ord-2446fb5909434dbaa40d4f451f844b20

Source dataset

uspto-grants-2004_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06673976B1