Ethylene Oxide → HCID 57517649, compound

Temperature

5 °C

At first, 100.0 g (0.64 mol) of l-menthol and 42.7 g (0.32 mol) of anhydrous aluminum chloride were added into a reaction vessel and after replacement with nitrogen, 500 ml of toluene was further added to the vessel and stirred with the mixture under the ice-cooling condition to cool the resulting mixture to 5° C. And while the temperature of the solution being kept at 5 to 10° C., 57 g of ethylene oxide was further added. On completion of the supply, the mixture was stirred for one more hour at a room temperature to complete the reaction. Next, the reaction solution was cooled again and washed with 150 ml of 10% aqueous hydrochloric acid while being kept at 20° C. or lower. After the reaction solution was washed again with 50 ml of saturated sodium hydrogen carbonate aqueous solution and then with 100 ml of saturated brine, water therein was removed with sodium sulfate and the solvent was recovered under reduced pressure to obtain 123.1 g of crude l-menthyloxyethanol. The obtained product was distilled to isolate and recover 45.7 g of an unreacted raw material, l-menthol, and refine and isolate 60.8 g of an aimed product, l-menthyloxyethanol. Theoretical yield: 47.4% based on l-menthol.

1. temperaturecooling condition
2. custombeing kept at 5 to 10° C.
3. customthe reaction
4. temperatureNext, the reaction solution was cooled again
5. washwashed with 150 ml of 10% aqueous hydrochloric acid
6. customwhile being kept at 20° C.
7. washAfter the reaction solution was washed again with 50 ml of saturated sodium hydrogen carbonate aqueous solution
8. customwith 100 ml of saturated brine, water therein was removed with sodium sulfate
9. customthe solvent was recovered under reduced pressure

ORD record

ord-6e08c1269f264b228c5c06e7affd25eb

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07923585B2