Ethanol → Cyclohexanone, 2-(hydroxymethylene)-

Cyclohexanone (200 grams, 2.0 moles) is added dropwise over a period of 2.75 hours to a stirred mixture of sodium hydride (50% oil dispersion, 105 grams, 2.1 moles), ethyl formate (200 grams, 2.7 moles), anhydrous ethanol (5 ml) and hexane (3500 ml) at 20° C. under nitrogen. Stirring is continued at room temperature for an additional 20 hours at which time a quantity of water sufficient to dissolve the reaction mixture is added. The layers are separated and the organic phase is washed twice with 5% aqueous sodium hydroxide. The combined aqueous phases are acidified with 25% aqueous sulfuric acid, and extracted three times with hexane. The organic phase is then washed twice with water, and distilled through a 4" vigreaux column at a 1:1 reflux take off ratio from 1 g hydroquinone to yield 318 g (63% theory) 2-hydroxymethylenecyclohexanone. Bp 47°-48° C. at 0.5 mm.

1. additionis added
2. customThe layers are separated
3. washthe organic phase is washed twice with 5% aqueous sodium hydroxide
4. extractionextracted three times with hexane
5. washThe organic phase is then washed twice with water
6. distillationdistilled through a 4" vigreaux column at a 1:1
7. temperaturereflux

ORD record

ord-ecf0e780a89e4338bc5c3b3020ee46d2

Source dataset

uspto-grants-1980_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04183363