Propionyl chloride → 2.2-Dimethyl-4-hydroxy-3-pentanone

HRID 1033613Notes

Reaction equation

HRID 1033613 reaction equation
[C:1](Cl)(=[O:4])[CH2:2][CH3:3].[C:6]([Mg]Cl)([CH3:9])([CH3:8])[CH3:7].C([O-])(O)=[O:13].[Na+]>C(OCC)C>[CH3:7][C:6]([CH3:9])([C:1](=[O:4])[CH:2]([OH:13])[CH3:3])[CH3:8]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 178418310HCID 178418310, compound

Product 1

HCID 111593452.2-Dimethyl-4-hydroxy-3-pentanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.24 g of cuprous chloride was suspended in 100 mL diethyl ether and then 22.1 g of propionyl chloride was added. The reaction was heated to reflux and 88 mL of t-butyl magnesium chloride was added slowly to maintain reflux. The reaction was stirred overnight then poured into 200 g ice and the pH adjusted to 8 with solid NaHCO3. The reaction was extracted with ether, washed with 10% aq. NaHCO3, water and then brine followed by MgSO4 drying. The product was purified by distillation to give 12.5 g of the ketone.

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. temperatureto maintain
  4. temperaturereflux
  5. extractionThe reaction was extracted with ether
  6. washwashed with 10% aq. NaHCO3, water
  7. distillationThe product was purified by distillation

Sources & evidence

ORD record
ord-08f9fff93a1d4a9c888b1790251bc517
Source dataset
uspto-grants-1994_05
Patent number
US05310929

Reaction notes

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