epsilon-CAPROLACTONE → 5299-61-6

To a well-stirred reaction vessel equipped with a thermometer and a pH electrode were added 17.1 g of 6-hexanolactone, 16 g of water, and 24 g of a 25 wt % aqueous NaOH solution. The mixture was stirred for 30 min while cooling down slowly. The sodium 6-hydroxyhexanoate solution formed was cooled to 4° C. and to this solution 70 mg of N-methylmorpholine was added. Then, 16.2 g of isopropyl chloroformate was added in 2 min. The reaction mixture was stirred for 90 min at 10° C. Chloroformate level in the organic layer was low and mixed anhydride was formed according to analysis by FT-IR. The water layer was separated and 19.3 g of a 70 wt % aqueous tert-butyl hydroperoxide solution (ex Lyondell) was added. With stirring, 0.5 g of Na2CO3 was added and 12.5 g of a 25 wt % aqueous NaOH solution was dosed in 20 min at 10° C. The reaction mixture was stirred for 60 min at 10° C. For a fast layer separation some water and diethyl ether were added. The water layer was separated and the organic layer was extracted with an aqueous sodium sulfite solution in order to reduce all hydroperoxide present. The organic layer was washed with an aqueous NaHCO3 solution to a neutral pH and the product was dried over MgSO4. After removal of the ether in vacuum at 20° C. a colourless liquid was obtained with a perester content of 92% in a yield of 62% based on the starting chloroformate.

1. customTo a well-stirred reaction vessel
2. customequipped with a thermometer
3. temperaturewhile cooling down slowly

ORD record

ord-c927458998b842d7aa5ebf0a222a6c72

Source dataset

uspto-grants-2003_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06610880B1