Acetaldehyde → HCID 18929411, compound

HRID 1598504Notes

Reaction equation

HRID 1598504 reaction equation
C([Li])CCC.Br[C:7]1[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=1[Cl:18].[CH:19](=[O:21])[CH3:20]>CCOCC>[Cl:18][C:8]1[CH:9]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:11]=[C:12]([Cl:13])[C:7]=1[CH:19]([OH:21])[CH3:20]

Participants

5

Reactant 3

HCID 177AcetaldehydeHCID 12682564-Bromo-3,5-dichlorobenzotrifluorideHCID 178418339Butyllithium

Product 1

HCID 18929411HCID 18929411, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a mixture of 65.2 ml of n-butyllithium (1.61M in hexane) and 100 ml of anhydrous ether was added dropwise 29.3 g of 4-bromo-3,5-dichlorobenzotrifluoride (3) in 30 ml of anhydrous ether at -78° C., followed by stirring for 20 minutes. Subsequently, 6.2 ml of acetaldehyde in 50 ml of anhydrous ether was added dropwise to the mixture at the same temperature, followed by stirring at 0° C. Ice waster was added to the reaction mixture, followed by extraction with ether, drying over anhydrous magnesium sulfate and concentration under reduced pressure to give 23.5 g of the desired product in the form of a colorless oil (crude yield 90.7% ).

Workup

  1. stirringby stirring at 0° C
  2. additionIce waster was added to the reaction mixture
  3. extractionfollowed by extraction with ether
  4. dry with materialdrying over anhydrous magnesium sulfate and concentration under reduced pressure

Sources & evidence

ORD record
ord-19fa225dfb0f4dbd96abb58ca7f5d241
Source dataset
uspto-grants-1998_04
Patent number
US05739083

Reaction notes

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