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 30 min and subsequently admixed with 27 g (0.90 mol) of paraformaldehyde. After 30 min at −20° C., the mixture is stirred at 0° C. for a further 2 h. After the solvent has been removed at 20° C. and 20 mbar (approx. 250 ml), 100 ml of MTBE and 200 ml of saturated aqueous solution of ammonium chloride are added to the oily residue and 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 30 min
3. waitAfter 30 min at −20° C.
4. stirringthe mixture is stirred at 0° C. for a further 2 h
5. customAfter the solvent has been removed at 20° C.
6. addition20 mbar (approx. 250 ml), 100 ml of MTBE and 200 ml of saturated aqueous solution of ammonium chloride are added to the oily residue
7. stirringthe mixture is stirred at RT for 2 h
8. customThe organic phase is removed
9. extractionthe aqueous phase is re-extracted 1× with 100 ml of MTBE
10. concentrationthe combined organic phases are concentrated on a rotary evaporator
11. distillationThe crude product (97% conversion based on methyl 2-ethylhexanoate) can be purified by distillation

ORD record

ord-5479c804022a4c8a98235b7fe6ad4c98

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07268253B2