Formaldehyde → 3-Cyclohexene-1,1-dimethanol
Reaction equation
[CH2:1]=[O:2].[OH-].[Na+].[CH:5](=[O:12])[CH:6]1[CH2:11][CH2:10][CH:9]=[CH:8][CH2:7]1>>[C:6]1([CH2:1][OH:2])([CH2:5][OH:12])[CH2:11][CH2:10][CH:9]=[CH:8][CH2:7]1Participants
Conditions
- Temperature
- 25 °C
Procedure
One hundred (100) parts by weight of a formaldehyde aqueous solution (37 wt. % formaldehyde) was charged to a reactor. To this solution, cooled externally with an ice-water bath, was added 118 parts of an aqueous sodium hydroxide solution (25 wt. % sodium hydroxide) by several portions and the temperature of the reaction content was maintained at 20 to 30° C. This was followed by a slow addition of 54 parts of 1,2,5,6-tetrahydrobenzaldehyde at such a rate that the reaction content temperature did not exceed 55° C. After the exotherm dissipated, it was heated at 55° C. for two hours with an external heating. The product precipitated out of the solution upon cooling and was collected by suction filtration. The wet-cake was washed thoroughly in the funnel with copious amount of water (5×100 parts). The crude product was allowed to dry in air overnight and purified by a recrystallization from toluene. The final product was an off-white colored crystalline material (yield 70%. m.p.: 92-93° C.).
Workup
- temperatureTo this solution, cooled externally with an ice-water bath
- customdid not exceed 55° C
- temperatureit was heated at 55° C. for two hours with an external heating
- customThe product precipitated out of the solution
- temperatureupon cooling
- filtrationwas collected by suction filtration
- washThe wet-cake was washed thoroughly in the funnel with copious amount of water (5×100 parts)
- customto dry in air overnight
- custompurified by a recrystallization from toluene
Sources & evidence
- ORD record
- ord-4e07c60878954f928750eca72aab8cc1
- Source dataset
- uspto-grants-2002_09
- Patent number
- US06454965B1
Reaction notes
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