Formaldehyde → 3-Cyclohexene-1,1-dimethanol

Temperature

10 °C

To a 5-liter volume four-necked flask provided with a stirrer, a thermometer, a Dimroth condenser and a dropping funnel, 633.3 g (purity 92%, 19 mol) of paraformaldehyde dissolved in 1004.0 g of water was charged, 465.6 g of sodium hydroxide (purity 98.5%, 11.5 mol) dissolved in 1397.0 g of water were dropwise added. Next, the mixture was cooled in an ice bath to 10° C. and 880.7 g of 3-cyclohexene-1-carboaldehyde (purity 97%, 7.8 mol) was dropwise added over 1 hour to the mixture. After dropwise addition, the solution temperature was increased to 20° C. The mixture was stirred at that temperature for 1 hour, then the flask was immersed in a hot water bath and was further stirred at 55° C. for 1 hour. Next, the reaction mixture was cooled down to 15° C. in a water bath and the precipitated solid was obtained by filtration. The solid thus obtained was washed with water to obtain a wet crude crystal of 4,4-bis[(hydroxy)methyl]cyclohexene (II) in an amount of 1396.0 g.

1. customTo a 5-liter volume four-necked flask provided with a stirrer
2. additionwas charged
3. additionwere dropwise added
4. additionAfter dropwise addition
5. temperaturethe solution temperature was increased to 20° C
6. customthe flask was immersed in a hot water bath
7. stirringwas further stirred at 55° C. for 1 hour
8. temperatureNext, the reaction mixture was cooled down to 15° C. in a water bath
9. customthe precipitated solid was obtained by filtration
10. customThe solid thus obtained
11. washwas washed with water

ORD record

ord-6f169d433983404e810db5e6c3388109

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09156762B2