Dicyclopentadiene → HCID 59559136, compound
Reaction equation
[CH2:1]=[C:2]([CH2:5][CH2:6][CH3:7])[CH:3]=[O:4].[CH2:8]1[CH:12]2[CH:13]3C=CC([CH:11]2C=[CH:9]1)C3>>[CH2:5]([C:2]1([CH:3]=[O:4])[CH2:11][CH:12]2[CH2:13][CH:1]1[CH:9]=[CH:8]2)[CH2:6][CH3:7]Participants
Conditions
- Temperature
- 170 °C
Procedure
A 5-L flask fitted with an overhead stirrer and a condenser was charged with di-n-butylamine (75 g) and acetic acid (70 g). Formaldehyde solution in water (1.3 L, 37%) was added and the resulting solution was heated to 50° C. with stirring. Pentanal (1 Kg) was then fed in over about 2 hours. After the feed was completed the temperature was maintained at 50° C. for 1 hour and then cooled to room temperature. The reaction mixture was poured into a separatory funnel. The organic layer was washed with water and purified by distillation to yield 2-methylene pentanal (820 g). 2-Methylene pentanal (302 g) and dicyclopentadiene (244 g) were loaded into a 2-L autoclave. The autoclave was sealed and heated to 170° C. The reaction was monitored by Gas Chromatography (“GC”) analysis, which showed the completion after 3 hours. The reaction was cooled to room temperature. The crude product was purified by distillation to yield 2-propylbicyclo[2.2.1]hept-5-ene-2-carbaldehyde (136 g). Product 2-methylene pentanal had the following NMR spectral characteristics:
Workup
- customThe autoclave was sealed
- customafter 3 hours
- temperatureThe reaction was cooled to room temperature
- distillationThe crude product was purified by distillation
Sources & evidence
- ORD record
- ord-9da7eb22e86c4bde85b7de4e8edd68b6
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08466325B2
Reaction notes
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