Dichloromethane → HCID 13326550, compound

HRID 358529Notes

Reaction equation

HRID 358529 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[CH:6]1([CH:12]=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[Cl:14]CCl>[Cl-].[Zn+2].[Cl-]>[C:1]([O:13][CH:12]([Cl:14])[CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1)(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 16275CyclohexanecarboxaldehydeHCID 62324Propionyl chloride

Product 1

HCID 13326550HCID 13326550, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
-5 °C

Procedure

A stirred solution of 73 ml (0.84 mole) of propionyl chloride in 250 ml of dichloromethane was cooled to 0° C. (salt-ice bath) and treated portionwise with 94.2 g (0.84 mole) of freshly distilled cyclohexanecarboxaldehyde. After further cooling to -5° C., approximately 0.5 g of zinc chloride was added. The temperature rose gradually to 7° C. as a solid separated. The cooling bath was removed and while stirring was continued the reaction mixture was allowed to warm to room temperature (the solid gradually went into solution). After about 1 hour some additional zinc chloride was added; there was no further reaction. The solution was kept overnight at room temperature.

Workup

  1. customrose gradually to 7° C. as a solid
  2. customseparated
  3. customThe cooling bath was removed
  4. temperatureto warm to room temperature (the solid
  5. additionAfter about 1 hour some additional zinc chloride was added
  6. customno further reaction

Sources & evidence

ORD record
ord-4f88b5efe901411f90e91ba26db38559
Source dataset
uspto-grants-1984_08
Patent number
US04468519

Reaction notes

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