1,2-Dichloroethane → 3,3,4,4,4-Pentafluorobutan-2-yl 4-formylbenzoate

HRID 852841Notes

Reaction equation

HRID 852841 reaction equation
[C:1]([C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1)([OH:3])=[O:2].[F:12][C:13]([F:21])([C:17]([F:20])([F:19])[F:18])[CH:14](O)[CH3:15].C(Cl)CCl.CCCCCC>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH:8]([C:7]1[CH:10]=[CH:11][C:4]([C:1]([O:3][CH:14]([C:13]([F:21])([F:12])[C:17]([F:20])([F:19])[F:18])[CH3:15])=[O:2])=[CH:5][CH:6]=1)=[O:9]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 8058HexaneHCID 120884-Formylbenzoic acidHCID 789913,3,4,4,4-Pentafluorobutan-2-ol

Product 1

HCID 589307223,3,4,4,4-Pentafluorobutan-2-yl 4-formylbenzoateYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-carboxybenzaldehyde (21.9 g, 145.9 mmol), 3,3,4,4,4-pentafluoro-2-butanol (24.1 g, 146.9 mmol), EDC (33.5 g, 174.8 mmol) and DMAP (18.1 g, 148.1 mmol) was dissolved in DMF (60 ml) at rt. It was stirred for 36 h at rt. Hexane was added, it was washed with 1 N HCl, sat NaHCO3 and brine. The aqueous layers were extracted three times with hexane. It was dried over Na2SO4, filtered, concentrated, and the residue was purified by silica gel chromatography (ethyl acetate:hexane 1:10) to yield the desired aldehyde as a yellow oil (67%).

Workup

  1. washit was washed with 1 N HCl
  2. extractionThe aqueous layers were extracted three times with hexane
  3. dry with materialIt was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by silica gel chromatography (ethyl acetate:hexane 1:10)

Sources & evidence

ORD record
ord-16e04388104c42c7882c3b155ae028bf
Source dataset
uspto-grants-2007_08
Patent number
US07253208B2

Reaction notes

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