Cyclopropanecarbonyl chloride → tert-Butyl cyclopropanecarboxylate

HRID 655491Notes

Reaction equation

HRID 655491 reaction equation
[CH3:1][C:2]([O-:5])([CH3:4])[CH3:3].[K+].[CH:7]1([C:10](Cl)=[O:11])[CH2:9][CH2:8]1.C(=O)([O-])O.[Na+]>COC(C)(C)C>[C:2]([O:5][C:10]([CH:7]1[CH2:9][CH2:8]1)=[O:11])([CH3:4])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxide

Product 1

HCID 13676038tert-Butyl cyclopropanecarboxylateYield 99.8%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
2.5 °C

Procedure

219.1 g (1.91 mol, 1 eq.) potassium tert-butylate were suspended in 2.5 L tert-butyl methyl ether and cooled to 0-5° C. 200 g (1 eq.) cyclopropanecarbonyl chloride were added over 60 min, maintaining the temperature between 0-5° C. (ice-ethanol bath cooling). In-line FTIR reaction monitoring indicates a feed controlled reaction. The reaction mixture was stirred 30 min at 0-5° C. and 1 L of 5% aq. sodium hydrogencarbonate solution was added. The aqueous phase was separated and extracted with 500 ml tert-butyl methyl ether. The organic phases were washed with 500 ml half saturated aq. sodium chloride solution, combined and concentrated under reduced pressure (30° C./150 mbar) to provide 271 g of the title compound (91% yield corrected for 8% residual tert-butyl methyl ether).

Workup

  1. temperaturemaintaining the temperature between 0-5° C.
  2. customIn-line FTIR reaction monitoring
  3. customreaction
  4. customThe aqueous phase was separated
  5. extractionextracted with 500 ml tert-butyl methyl ether
  6. washThe organic phases were washed with 500 ml half saturated aq. sodium chloride solution
  7. concentrationconcentrated under reduced pressure (30° C./150 mbar)

Sources & evidence

ORD record
ord-de326d39b633418fbdf9750ae310c8b2
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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