Sulfuric Acid → 5H-Octafluoropentanoic acid

5.2 ml water, 19 ml MeCN, 0.34 g KBr, TEMPO (0.12 g), and 6 g of 2,2,3,3,4,4,5,5-octafluoro-pentan-1-ol were placed in a 100 mL glass flask equipped with a dropping funnel and stirrer. 45 mL of 15% (wt) aq. NaOCl buffered to pH 8-9 were added via the dropping funnel in 3 portions over two days while stirring at room temperature. Then concentrated sulphuric acid were added to render the reaction mixture acidic. (pH 1-2). The reaction mixture was extracted three times with diethyl ether and the combined organic phases were dried over magnesium sulphate. The solvent was evaporated to give a colorless liquid (8.98 g), which was distilled using a water pump (15 mmHg, 73° C.) to give 5.13 g of the acid. Yield: 80%. 1H NMR (CDCl3): 6.08 (tt, J=52 Hz, J=5.3 Hz, 1H); 8.6 (s, 1H); 19F NMR (CDCl3): −120.6 (t, J=9.2 Hz, 2F); −125.81 (m, 2F); −130.61 (m, 2F); −138.4 (dm, J=52 Hz, 2F).

1. customequipped with a dropping funnel and stirrer
2. additionwere added via the dropping funnel in 3 portions over two days
3. extractionThe reaction mixture was extracted three times with diethyl ether
4. dry with materialthe combined organic phases were dried over magnesium sulphate
5. customThe solvent was evaporated

ORDレコード

ord-b55ef902930d446496332faeba9a26a4

出典データセット

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08809580B2