Heptafluorobutanol → 4-(2,2,3,3,4,4,4-Heptafluorobutoxy)benzaldehyde

HRID 630311Notes

Reaction equation

HRID 630311 reaction equation
[F:1][C:2]([F:12])([C:5]([F:11])([F:10])[C:6]([F:9])([F:8])[F:7])[CH2:3][OH:4].F[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1.[H-].[Na+]>CN(C)C=O>[F:1][C:2]([F:12])([C:5]([F:10])([F:11])[C:6]([F:7])([F:8])[F:9])[CH2:3][O:4][C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 9776HeptafluorobutanolHCID 24758Sodium hydrideHCID 680234-Fluorobenzaldehyde

Product 1

HCID 539850394-(2,2,3,3,4,4,4-Heptafluorobutoxy)benzaldehydeYield 9.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Following the above procedure, a solution of 2,2,3,3,4,4,4-heptafluoro-1-butanol (750 μL, 6 mmol) in N,N-dimethylformamide (8 mL) and 4-fluorobenzaldehyde (429 μL, 4 mmol) were reacted together with sodium hydride (288 mg as 55-60% mineral oil dispersion, 6 mmol) in N,N-dimethylformamide (2 mL). Flash chromatography gave 117 mg of 4-(2,2,3,3,4,4,4-heptafluorobutoxy)benzaldehyde; 1H NMR (300 MHz, CDCl3) δ 9.93 (s, 1H), 7.89 (d, 2H), 7.08 (d, 2H), 4.54 (tt, 2H) ppm.

Sources & evidence

ORD record
ord-dec136fd129846f8b9a4df5ad452bb3b
Source dataset
uspto-grants-2016_04
Patent number
US09315509B2

Reaction notes

Loading…