Water → HCID 18433843, compound

HRID 2305825Notes

Reaction equation

HRID 2305825 reaction equation
[CH2:1]([C:3](=[CH:9][CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[OH-].[Na+].[CH:13]([Cl:16])(Cl)[Cl:14].O>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[Cl:14][C:13]1([Cl:16])[CH:1]([CH3:2])[C:3]1([CH2:9][CH3:10])[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

7

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 14798Sodium HydroxideHCID 54093674Ethyl 2-ethylbut-2-enoate

Product 1

HCID 18433843HCID 18433843, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
40 °C

Procedure

38 g (0.27 mol) of ethyl 2-ethylbut-2-enoate, 2.2 g (0.01 mol) of benzyltriethylammonium chloride and 57 ml of 50% strength aqueous sodium hydroxide solution were initially charged in 180 ml of dichloromethane. At 35° C. -40° C., 95 ml of chloroform were added dropwise over a period of 1 hour. After a reaction time of 5 hours at 40° C., the mixture was stirred at room temperature for a further 14 hours. For work-up, the reaction solution was poured into 1.5 l of water. The organic phase was removed and the aqueous phase was then extracted with dichloromethane. The combined organic phases were washed with water and, after drying with magnesium sulfate, concentrated. The residue (47 g) was subjected to vacuum distillation. The title compound was isolated as a colorless liquid (25.7 g, 43% yield, boiling point 71° C. at 2 mbar).

Workup

  1. customThe organic phase was removed
  2. extractionthe aqueous phase was then extracted with dichloromethane
  3. washThe combined organic phases were washed with water
  4. dry with materialafter drying with magnesium sulfate
  5. concentrationconcentrated
  6. distillationThe residue (47 g) was subjected to vacuum distillation

Sources & evidence

ORD record
ord-b6638f4efac14d5f9eb8e2599337692d
Source dataset
uspto-grants-2002_08
Patent number
US06441044B1

Reaction notes

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