Cyclopropanecarbonyl chloride → tert-Butyl cyclopropanecarboxylate

Participants

Reaction Conditions

Reaction Steps

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).

Provenance & Evidence