1-Chloro-3-methyl-2-butene → HCID 53898318, compound
Reaction equation
[OH-].[Na+].[CH2:3]([C:6](=[CH:9][CH2:10][CH3:11])[C:7]#[N:8])[CH2:4][CH3:5].[CH2:12](Cl)[CH:13]=[C:14]([CH3:16])[CH3:15]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH3:15][C:14]([CH3:16])=[CH:13][CH2:12][C:6]([CH:3]=[CH:4][CH3:5])([CH2:9][CH2:10][CH3:11])[C:7]#[N:8]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 75 °C
Procedure
In analogy to Example 1, 64 g (1.6 moles) of NaOH, 200 ml of toluene, and 15 g of tetrabutylammonium bromide were first introduced and heated to 75° C. To this mixture was added a mixture of 147.6 g (1.2 moles) of 2-propyl-2-pentenenitrile and 157 g (1.5 moles) of prenyl chloride within 2 hours in individual doses. The reaction mixture was further heated for 3 hours at 85° C. and subsequently processed according to Example 1. The yield in desired product was 103 g, corresponding to 44.9% of the theoretical.
Workup
- additionTo this mixture was added
- temperatureThe reaction mixture was further heated for 3 hours at 85° C.
Sources & evidence
- ORD record
- ord-e7522f9694574478b41c4fbcc1c1bc88
- Source dataset
- uspto-grants-1986_11
- Patent number
- US04625046
Reaction notes
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