4'-Hydroxyacetophenone → 1-(4-Hydroxyphenyl)heptane-1,3-dione

Temperature

8 °C

Sodium tert-butoxide, 1270 g, is slurried in 1390 g THF and the mixture heated to reflux temperature. A solution of 580 g 4-hydroxyacetophenone and 555 g ethylvalerate in 1390 g THF is added over 30 minutes. The solution is stirred at reflux temperature until the reaction is complete, ca 4.5 h, and then quenched by addition of the reaction mixture to 1270 g 37% HCl. The mixture is concentrated by distillation of THF at reduced pressure and to the residue is added 900 g toluene. The water phase is separated and the toluene phase washed with 900 g 10% aqueous NaCl. The toluene is stripped at reduced pressure and the residual oil diluted with 850 g acetic acid. The solution is cooled to 8° C. and 850 ml water added slowly. The formed slurry is stirred at 5-8° C. for 90 minutes and then filtered and washed with 608 g 20% aqueous acetic acid. Drying under vacuum at 40° C. gives 608 g 1-(4-hydroxyphenyl)-1,3-heptandione.

1. temperaturethe mixture heated
2. temperatureto reflux temperature
3. temperatureat reflux temperature until the reaction
4. waitis complete, ca 4.5 h
5. customquenched by addition of the reaction mixture to 1270 g 37% HCl
6. concentrationThe mixture is concentrated by distillation of THF at reduced pressure and to the residue
7. additionis added 900 g toluene
8. customThe water phase is separated
9. washthe toluene phase washed with 900 g 10% aqueous NaCl
10. additionthe residual oil diluted with 850 g acetic acid
11. addition850 ml water added slowly
12. stirringThe formed slurry is stirred at 5-8° C. for 90 minutes
13. filtrationfiltered
14. washwashed with 608 g 20% aqueous acetic acid
15. customDrying under vacuum at 40° C.

ORD record

ord-4e5638e25db34bbf9043eaae42f169b9

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519165B2