Hydrochloric Acid → alpha-Allenyl-3-phenoxybenzyl alcohol
Reaction equation
[C:1]([CH:3]([OH:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)#[CH:2].C=O.[CH:20](NC(C)C)(C)C.Cl>O1CCOCC1>[CH:1]([CH:3]([OH:17])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([O:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:5]=1)=[C:2]=[CH2:20]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
10 g of α-ethynyl-3-phenoxybenzyl alcohol, 2.1 g of paraformaldehyde, 5.3 g of diisopropylamine, 0.215 g of CuBr and 50 ml of dioxane are refluxed for 2 hours. The reaction mixture is cooled to 20° C., poured into a solution of 2 N HCl and extracted with ether. The organic phase is washed with 10% potassium carbonate and saturated sodium chloride solution, dried over magnesium sulfate and concentrated. The residue is chromatographed over silica gel with a 7:3 mixture of hexane/ether as eluant, affording the compound of the formula ##STR5## with a refractive index of nD20° =1.5942.
Workup
- extractionextracted with ether
- washThe organic phase is washed with 10% potassium carbonate and saturated sodium chloride solution
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- customThe residue is chromatographed over silica gel with a 7:3 mixture of hexane/ether as eluant
- customaffording the compound of the formula ##STR5## with a refractive index of nD20° =1.5942
Sources & evidence
- ORD record
- ord-bef36a2472e643a9af1854f541dd8bdf
- Source dataset
- uspto-grants-1982_09
- Patent number
- US04348408
Reaction notes
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