Allyl bromide → HCID 22227278, compound
Reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([CH2:13][CH2:14][OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][C:19](C)([O-])[CH3:20].[K+].C(Br)C=C>CS(C)=O>[CH2:20]([O:15][CH2:14][CH2:13][C:12]1[CH:11]=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=1)[CH:19]=[CH2:18]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
A reaction flask was charged with 4-benzyloxy phenethyl alcohol of formula (6), (12 g, 0.052 mol), potassium tert-butoxide (8.842 g, 0.079 ml) and 50 ml and DMSO. The mixture was stirred under nitrogen at 50° C. for 30 minutes. A solution of allyl bromide (6.8 ml, 0.079 mol) was added drop wise to the reaction mixture with cooling about 20–25° C. The mixture was then stirred at 50° C. for 2 h. and cooled to room temperature. The reaction mixture was subsequently quenched with 150 ml of water. The desired product was extracted from neutralized aqueous mixture with toluene. The toluene extract was then washed with water and concentrated under vacuum to afford the title compound of formula (7), 13.9 g, (98%).
Workup
- temperaturewith cooling about 20–25° C
- stirringThe mixture was then stirred at 50° C. for 2 h.
- temperaturecooled to room temperature
- customThe reaction mixture was subsequently quenched with 150 ml of water
- extractionThe desired product was extracted from neutralized aqueous mixture with toluene
- extractionThe toluene extract
- washwas then washed with water
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-e848b7d491d046428efb2c46b23ffb9a
- Source dataset
- uspto-grants-2006_03
- Patent number
- US07019172B2
Reaction notes
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