Dimethylformamide → 3-Chloro-3-[3-chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]propenal

HRID 1018807Notes

Reaction equation

HRID 1018807 reaction equation
C(Cl)(=O)C([Cl:4])=O.CN(C)[CH:9]=[O:10].[Cl:12][C:13]1[CH:14]=[C:15]([C:29](=O)[CH3:30])[CH:16]=[CH:17][C:18]=1[CH:19]1[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]1.[O-]CC.[Na+]>ClCCl>[Cl:4][C:29]([C:15]1[CH:16]=[CH:17][C:18]([CH:19]2[CH2:24][C:23]([CH3:26])([CH3:25])[CH2:22][C:21]([CH3:28])([CH3:27])[CH2:20]2)=[C:13]([Cl:12])[CH:14]=1)=[CH:30][CH:9]=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 2723922Sodium ethoxideHCID 223904251-[3-Chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone

Product 1

HCID 572145173-Chloro-3-[3-chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]propenal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3.51 ml of oxalyl chloride are added dropwise at a temperature of between −5° C. and 2° C. to a solution of 3.72 ml of dimethylformamide and 20 ml of anhydrous dichloromethane and the reaction mixture is then stirred at room temperature for 30 minutes. 3.92 g of 1-[3-chloro-4-(3,3,5,5-tetramethylcyclohexyl)phenyl]ethanone (compound V.6) dissolved in 10 ml of dichloromethane are then added rapidly, after which the reaction mixture is stirred at room temperature for 12 hours. The reaction mixture is poured into a water/ice mixture and 20 ml of aqueous 2.84 M sodium ethoxide solution are then added. The resulting mixture is washed with 50 ml of sodium hydrogen carbonate solution and 50 ml of water, the phases are separated after settling has taken place, the organic phase is dried over magnesium sulphate and the solvents are evaporated off under reduced pressure. The oil obtained is purified by chromatography on a column of silica gel, eluting with a 97/3 (v/v) cyclohexane/ethyl acetate mixture.

Workup

  1. additionare then added rapidly
  2. stirringafter which the reaction mixture is stirred at room temperature for 12 hours
  3. additionare then added
  4. washThe resulting mixture is washed with 50 ml of sodium hydrogen carbonate solution and 50 ml of water
  5. customthe phases are separated after settling
  6. dry with materialthe organic phase is dried over magnesium sulphate
  7. customthe solvents are evaporated off under reduced pressure
  8. customThe oil obtained
  9. customis purified by chromatography on a column of silica gel
  10. washeluting with a 97/3 (v/v) cyclohexane/ethyl acetate mixture

Sources & evidence

ORD record
ord-f8dedd069e3949489c2edd6a2d370b42
Source dataset
uspto-grants-2002_11
Patent number
US06482986B1

Reaction notes

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