Chloroacetyl chloride → 4-Chloro-2,2-dimethyl-3-oxobutanal

HRID 1253133Notes

Reaction equation

HRID 1253133 reaction equation
O1CCN([CH:7]=[C:8]([CH3:10])[CH3:9])CC1.[Cl:11][CH2:12][C:13](Cl)=[O:14].C(=O)(O)[O-:17].[Na+]>C(OCC)C>[Cl:11][CH2:12][C:13](=[O:14])[C:8]([CH3:9])([CH3:10])[CH:7]=[O:17]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 102255Morpholine, 4-(2-methyl-1-propenyl)-HCID 516892Sodium Bicarbonate

Product 1

HCID 132699644-Chloro-2,2-dimethyl-3-oxobutanalYield 61%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

210 g (1.5 mols) of 1-morpholino-2-methyl-prop-1-ene are added dropwise, in the course of one hour, to 169.0 g (1.5 mols) of chloroacetyl chloride, dissolved in 350 ml of diethyl ether, at 5° C. After the addition is complete, the mixture is stirred for a further 3 hours under reflux. The solution is poured onto 100 g of ice and brought to pH 5 with aqueous sodium bicarbonate solution, and the ether phase is separated off. The aqueous phase is extracted with 100 ml of diethyl ether, the organic phases are combined, and dried over sodium sulphate, the solvent is distilled off and the residue is distilled under the vacuum from a water jet. 136.4 g (61% of theory) of 4-chloro-3-keto-2,2-dimethylbutanal of boiling point 95°-98° C./14 mbar are obtained.

Workup

  1. additionAfter the addition
  2. temperatureunder reflux
  3. customthe ether phase is separated off
  4. extractionThe aqueous phase is extracted with 100 ml of diethyl ether
  5. dry with materialdried over sodium sulphate
  6. distillationthe solvent is distilled off
  7. distillationthe residue is distilled under the vacuum from a water jet

Sources & evidence

ORD record
ord-6ce79ee19f1d45c2bcbccd8a46fa2b69
Source dataset
uspto-grants-1988_05
Patent number
US04747869

Reaction notes

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