Sodium Hydroxide → Decyl glycidyl ether

Participants

Reaction Conditions

Reaction Steps

To the crude 1-chloro-3-decyloxy-2-propanol prepared as described above and cooled to 40° C. was added NaOH (50% aqueous, 76 g, 2.2 mole) and water (44 g). The temperature rose to 50° C., then the mixture was heated to 85°-90° C. for three hours. Analysis by GC showed the crude product contained 11% unreacted alcohol and 75% of the expected epoxide. Water (200 ml) was added to dissolve precipitated salt. The aqueous phase was separated (pH 4) and the organic phase washed with 5% NaCl solution to pH 7-8 (2×400 ml). The crude product (435 g, 102%) was fractionally distilled at 12 mmHg to yield 286 g of (decyloxy)methyloxirane (67% overall based on epichlorohydrin). GC showed the product was 97% pure.

Provenance & Evidence