Sulfuric Acid → 3,3,4,4,5,5,5-Heptafluoro-2-methylpentan-2-ol

HRID 487835

Reaction equation

HRID 487835 reaction equation
FC(F)(F)C(F)(F)C(F)(F)C(OC)=[O:6].S(=O)(=O)(O)O.[CH3:20][C:21]([C:23]([F:32])([F:31])[C:24]([F:30])([F:29])[C:25]([F:28])([F:27])[F:26])=[CH2:22]>[Rh]>[CH3:22][C:21]([OH:6])([C:23]([F:31])([F:32])[C:24]([F:29])([F:30])[C:25]([F:26])([F:27])[F:28])[CH3:20].[CH3:22][CH:21]([C:23]([F:31])([F:32])[C:24]([F:29])([F:30])[C:25]([F:26])([F:27])[F:28])[CH3:20]

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 67741Methyl 2,2,3,3,4,4,4-heptafluorobutanoateHCID 19091131HCID 19091131, compound

Product 2

HCID 5404793,3,4,4,5,5,5-Heptafluoro-2-methylpentan-2-olHCID 19091139HCID 19091139, compound

Reagents, catalysts & solvents 1

HCID 23948RhodiumCatalyst

Procedure

Following the procedure of E. T. McBee et al. ibid, 2-methyl-3,3,4,4,5,5,5-heptafluoro-pentan-2-ol was prepared by adding methyl heptafluorobutyrate to 2 equivalents of methyl Grignard. The alcohol (boiling point 108° C.) was dehydrated with concentrated sulfuric acid to 2-methyl-3,3,4,4,5,5,5-heptafluoro-pent-1-ene (boiling point 55° C.). Hydrogenation of this olefin at 1500 psig using 5% rhodium/carbon gave 2-methyl-3,3,4,4,5,5,5-heptafluoropentane, boiling point 59°-61° C. 1H NMR (CDCl3)δ 1.2 (d, 6 Hz), 2.45 (m). This compound was miscible with silicone oil with a perfluorinated polyether at 25° C. and with light mineral oil at 56° C.

Sources & evidence

ORD record
ord-eb7b9f58b1a643fc86084c6992c7e191
Source dataset
uspto-grants-1994_03
Patent number
US05298083

Linked notes

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