Acetic Acid → 1-Nonen-4-ol
Reaction equation
[CH:1](=[O:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:8](Cl)[CH:9]=[CH2:10].[Sn](Cl)Cl.[I-].[Na+].C(O)(=O)C.[Al]>[Cu].O>[OH:7][CH:1]([CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:10][CH:9]=[CH2:8]Participants
9
Reactant 6
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 35 °C
Procedure
To 500 ml water was added 100 g hexanal (1 mol), 184 g allylchloride (2.4 mol), 19 g tin(II) chloride (0.1 mol), 1.5 g sodium iodide (0.01 mol), 12.5 g copper powder (0.2 mol), 108 g acetic acid (1.8 mol) and 32.4 g aluminium (1.2 mol) (e.g. foil or clips). The reaction mixture was stirred vigorously for ca. 12 h at 35° C. Then the reaction mixture was separated as an aqueous and an organic layer, and the organic layer was distilled in vacuo to give 4-hydroxy-1-nonene (the conversion of starting material (based on hexanal) is typically better than 95%).
Workup
- customThen the reaction mixture was separated as an aqueous and an organic layer
- distillationthe organic layer was distilled in vacuo
Sources & evidence
- ORD record
- ord-807dba5b286743ca8f902843bcfb3a8a
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07683187B2
Reaction notes
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