Hydrochloric Acid → 2-ethyl-2-(hydroxymethyl)hexanoic Acid

Temperature

0 °C

27 ml (72.9 mmol) of n butyllithium (2.7 M in heptane) are added dropwise at 0° C. to a solution of 10.9 ml of diisopropylamine (77.5 mmol) in 60 ml of THF, and the mixture is stirred at 0° C. for 30 min. Within 10 min, 5 g (34.7 mmol) of 2-ethylhexanoic acid are added dropwise at 0° C. and the reaction mixture is heated to 50° C. for 1.5 h. The clear solution is cooled to 0° C. and admixed with 3.1 g (103 mmol) of paraformaldehyde. After 10 min at 0° C., the mixture is stirred at RT for 18 h. The mixture is admixed with saturated aqueous solution of ammonium chloride and adjusted to pH=1-2 with 6N of HCl. The organic phase is removed, the aqueous phase is re-extracted once with MTBE and the combined organic phases are concentrated on a rotary evaporator. The yield of pure product is 89% (GC).

1. waitWithin 10 min
2. temperaturethe reaction mixture is heated to 50° C. for 1.5 h
3. temperatureThe clear solution is cooled to 0° C.
4. waitAfter 10 min at 0° C.
5. stirringthe mixture is stirred at RT for 18 h
6. customThe organic phase is removed
7. extractionthe aqueous phase is re-extracted once with MTBE
8. concentrationthe combined organic phases are concentrated on a rotary evaporator

ORD record

ord-8676f939d54e4755ab22cdc1f584ee33

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07268253B2