Formaldehyde → 3-Hydroxy-2,2-dimethylpropyl hydroxypivalate

Temperature

60 °C

101 g (1.25 mol) of 37% strength aqueous formaldehyde solution and 99 g (1.37 mol) of isobutyraldehyde were mixed at 40° C. under nitrogen with 4.2 g (0.03 mol) of 40% strength aqueous trimethylamine solution by stirring. The temperature of the mixture rose to 93° to 94° in the course of from 15 to 20 minutes. The mixture was stirred at that temperature for a further 10 minutes, and the trimethylamine, excess isobutyraldehyde and 58 g of water were then distilled off under reduced pressure. The remaining solution of hydroxypivalinaldehyde was then cooled down to 60° C., and 1.9 g (0.025 mol) of finely pulverulent calcium hydroxide were then added with vigorous stirring. After the exothermic reaction had ceased and a further, short period of stirring, 2.5 g (0.054 mol) of 100% strength formic acid were added at 70° C., and the mixture was stirred 70° C. for 10 minutes. The aqueous phase was then separated off, and the organic phase was subjected to fractional distillation. 110 g (0.54 mol) were isolated of 2,2-dimethyl-1,3-propanediol hydroxypivalate, corresponding to 86.5% of theory, based on starting formaldehyde.

1. customrose to 93° to 94° in the course of from 15 to 20 minutes
2. stirringThe mixture was stirred at that temperature for a further 10 minutes
3. distillationthe trimethylamine, excess isobutyraldehyde and 58 g of water were then distilled off under reduced pressure
4. addition1.9 g (0.025 mol) of finely pulverulent calcium hydroxide were then added with vigorous stirring
5. customAfter the exothermic reaction
6. stirringa further, short period of stirring
7. stirringthe mixture was stirred 70° C. for 10 minutes
8. customThe aqueous phase was then separated off
9. distillationthe organic phase was subjected to fractional distillation

ORD record

ord-34359c4966084c9f859c27d79cb23210

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04837357