Ethanol → HCID 54332237, compound

HRID 1089898Notes

Reaction equation

HRID 1089898 reaction equation
[OH-].[Na+].[C:3]([C:6]1([S:9][CH2:10][CH2:11][CH3:12])[CH2:8][CH2:7]1)(=[O:5])[CH3:4].[Cl:13][C:14]1[CH:21]=[C:20]([Cl:22])[CH:19]=[CH:18][C:15]=1[CH:16]=O.C(O)C>O.ClCCl>[CH2:10]([S:9][C:6]1([C:3]([CH:4]=[CH:16][C:15]2[CH:18]=[CH:19][C:20]([Cl:22])=[CH:21][C:14]=2[Cl:13])=[O:5])[CH2:8][CH2:7]1)[CH2:11][CH3:12]

Participants

7

Reactant 4

HCID 702EthanolHCID 134042,4-DichlorobenzaldehydeHCID 14798Sodium HydroxideHCID 14348392HCID 14348392, compound

Product 1

HCID 54332237HCID 54332237, compoundYield 97.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5 pellets of solid sodium hydroxide are added at room temperature to a mixture of 41.7 g (0.26 mol) of 1-acetyl-1-propylmercapto-cyclopropane, 46 g (0.26 mol) of 2,4-dichlorobenzaldehyde, 130 ml of ethanol and 30 ml of dichloromethane. The mixture is stirred for a further 14 hours at room temperature. 50 ml of water are added, and the oil phase is separated off and taken up in dichloromethane. The organic phase is washed using water, dried over sodium sulphate and concentrated by stripping off the solvent under reduced pressure. In this manner, 80 g (97% of theory) of 2,4-dichlorophenyl-ethenyl 1-propylmercaptocyclopropyl ketone (cis-trans isomers) are obtained in the form of an oily product.

Workup

  1. customthe oil phase is separated off
  2. washThe organic phase is washed
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6b25381997a84b0ab85338ae41428034
Source dataset
uspto-grants-1992_01
Patent number
US05079374

Reaction notes

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