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

HRID 2080702Notes

Reaction equation

HRID 2080702 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-0e95271d66ec49f88794be995e20835b
Source dataset
uspto-grants-2011_04
Patent number
US07932405B2

Reaction notes

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