Cyclopropanecarbonyl chloride → tert-Butyl cyclopropanecarboxylate

HRID 1096174Notes

Reaction equation

HRID 1096174 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+]>CC(OC)(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 99.6%

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
2.5 °C

Procedure

219.1 g (1913 mmol, 1 eq.) potassium tert-butylate were suspended in 2.5 L TBME 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-EtOH 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. NaHCO3 solution was added. The aqueous phase was separated and extracted with 500 ml TBME. The organic phases were washed with 500 ml half sat. aq. NaCl 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 TBME).

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 TBME
  6. washThe organic phases were washed with 500 ml half sat. aq. NaCl solution
  7. concentrationconcentrated under reduced pressure (30° C./150 mbar)

Sources & evidence

ORD record
ord-8c0efe3ff5294e369b80b978af47f90a
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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