Acetic Acid → HCID 13046233, compound

A mixture of 1.00 g of (E)-4(3-hydroxyphenoxy)-2-methyl-2-buten-1-al, 7.31 g active manganese dioxide, 1.26 g sodium cyanide and 0.4 g glacial acetic acid in 40 ml methanol is stirred at room temperature for about 16 hours, filtered and the filtrate evaporated to dryness using an aspirator and a concentrated aqueous sodium hydroxide trap. During the volume reduction, the filtrate is stirred in a water bath at about 35° C. The red oil residue is treated with 50 ml diethylether and 50 ml distilled water and the mixture stirred vigorously for about one hour. The phases are separated and the water layer is washed with 50 ml diethylether. The organic layers are combined and washed with two 150 ml portions of distilled water. The ether layer is dried over anhydrous magnesium sulfate, treated with activated charcoal and filtered. The filtrate is evaporated to dryness to yield 0.68 g light yellow oil which crystallizes on standing which is taken up in 40 ml diethylether and heated under a stream of nitrogen as 15 ml hexanes is slowly added. When the volume reaches 25 ml, it is treated with activated charcoal and filtered. The filtrate is reduced in volume to 200 ml, allowed to cool to room temperature and is placed in a freezer. Bright yellow solid forms and is collected by nitrogen pressure filtration and is dried under a stream of nitrogen yielding 0.27 g product, m.p. 79°-81° C. Elemental Analysis. Calculated: C,64.85; H,6.35. Found: C,64.74; H,6.37.

1. filtrationfiltered
2. customthe filtrate evaporated to dryness
3. stirringDuring the volume reduction, the filtrate is stirred in a water bath at about 35° C
4. additionThe red oil residue is treated with 50 ml diethylether and 50 ml
5. distillationdistilled water
6. stirringthe mixture stirred vigorously for about one hour
7. customThe phases are separated
8. washthe water layer is washed with 50 ml diethylether
9. washwashed with two 150 ml portions of distilled water
10. dry with materialThe ether layer is dried over anhydrous magnesium sulfate
11. additiontreated with activated charcoal
12. filtrationfiltered
13. customThe filtrate is evaporated to dryness
14. customto yield 0.68 g light yellow oil which
15. customcrystallizes on standing which
16. temperatureheated under a stream of nitrogen as 15 ml hexanes
17. additionis slowly added
18. additionis treated with activated charcoal
19. filtrationfiltered
20. temperatureto cool to room temperature
21. filtrationBright yellow solid forms and is collected by nitrogen pressure filtration
22. customis dried under a stream of nitrogen yielding 0.27 g product, m.p. 79°-81° C

ORD record

ord-8b174e314ef44aadb201e0b65d0ccf36

Source dataset

uspto-grants-1982_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04340765