Formaldehyde → HCID 23124995, compound

Temperature

-20 °C

47 ml (0.334 mol) of diisopropylamine are added dropwise at −20° C. to a solution of 118 ml (0.319 mol) of n-butyllithium (2.7 M in heptane) in 118 ml of THF, and the mixture is stirred at −20° C. for 30 min. Within approx. 15 min, 48 g (0.304 mol) of methyl 2-ethylhexanoate are added dropwise at −20° C., and the mixture is stirred at −20° C. for a further 30 min and subsequently admixed with 18 g (0.60 mol) of paraformaldehyde. After 30 min at −20° C., the mixture is stirred at 0° C. for 2 h. After addition of 100 ml of MTBE and 100 ml of saturated aqueous solution of ammonium chloride, the mixture is stirred at RT for 2 h. The organic phase is removed, the aqueous phase is re-extracted 1×with 100 ml of MTBE and the combined organic phases are concentrated on a rotary evaporator. The crude product (97% conversion based on methyl 2-ethylhexanoate) can be purified by distillation to obtain methyl 2-ethyl-2-hydroxymethylhexanoate (b.p.: 100° C., 6 mbar) in 91% yield with a purity of >99%.

1. waitWithin approx. 15 min
2. stirringthe mixture is stirred at −20° C. for a further 30 min
3. waitAfter 30 min at −20° C.
4. stirringthe mixture is stirred at 0° C. for 2 h
5. stirringthe mixture is stirred at RT for 2 h
6. customThe organic phase is removed
7. extractionthe aqueous phase is re-extracted 1×with 100 ml of MTBE
8. concentrationthe combined organic phases are concentrated on a rotary evaporator
9. distillationThe crude product (97% conversion based on methyl 2-ethylhexanoate) can be purified by distillation

ORD record

ord-bf875008833e47d7855dba542b09d8a6

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07268253B2