2-Methoxypropene → 6,10,14-Trimethylpentadeca-3,5-dien-2-one
Reaction equation
[CH3:1][C:2](O)([CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])[C:3]#[CH:4].C[O:18][C:19]([CH3:21])=[CH2:20].OS([O-])(=O)=O.[K+]>O>[CH3:1][C:2]([CH2:5][CH2:6][CH2:7][CH:8]([CH3:15])[CH2:9][CH2:10][CH2:11][CH:12]([CH3:14])[CH3:13])=[CH:3][CH:4]=[CH:20][C:19](=[O:18])[CH3:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
190 g of 3,7,11-trimethyldodec-1-yn-3-ol (purity 95%, 0.848 mol) and 200 g of 2-methoxypropene (2.78 mol) and 0.58 g of KHSO4, dissolved in 1.74 g of water, were introduced into a pressure-resistant vessel. The reactor was flushed with nitrogen and closed. After a reaction time of 1 hour at 120° C., the mixture was cooled to about 50° C. and a further 0.58 g of KHSO4, dissolved in 1.74 g of water, was added. The mixture was once again heated to 120° C. After a reaction time of one hour, the reaction was complete. Distillation was carried out as in Example 1.147 g of a mixture comprising mainly 2-methoxypropene and 2,2-dimethoxypropane and 213 g of a fraction comprising 1.6% of 3,7,11-trimethyldodec-1-yn-3-ol, 67% of 6,10,14-trimethylpentadeca-4,5-dien-2-one, and 7.3% of 6,10,14-trimethylpentadeca-3,5-dien-2-one were obtained.
Workup
- additionwere introduced into a pressure-resistant vessel
- customThe reactor was flushed with nitrogen
- customclosed
- dissolutiona further 0.58 g of KHSO4, dissolved in 1.74 g of water
- additionwas added
- temperatureThe mixture was once again heated to 120° C
- customAfter a reaction time of one hour
- distillationDistillation
Sources & evidence
- ORD record
- ord-3df2a969f3db4b34af3d4bfafc9da65d
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06184420B2
Reaction notes
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