Benzene, (3-chloro-1-propenyl)- → 4-[(4-Ethenylphenyl)methoxy]butan-1-OL
Reaction equation
[CH:1]([OH:6])(O)[CH2:2][CH2:3][CH3:4].[O-:7][CH2:8][CH2:9][CH2:10][CH3:11].[K+].Cl[CH2:14][CH:15]=[CH:16][C:17]1C=CC=C[CH:18]=1>>[OH:7][CH2:8][CH2:9][CH2:10][CH2:11][O:6][CH2:1][C:2]1[CH:3]=[CH:4][C:16]([CH:17]=[CH2:18])=[CH:15][CH:14]=1Participants
Procedure
Butanediol (40 ml; 40.68 g; 0.452 mol) was stirred in a 100 ml round bottomed flask, and treated portion wise with potassium butoxide (17.60 g; 0.144 mol). The initial reaction was exothermic. The reaction mixture was stirred for 1.5 hours at room temperature. The resulting cloudy solution was then treated with chloromethyl styrene (20.00 g; 0.131 mol). The styrene formed an upper, pale green layer, (the colouration being due to the presence of inhibitor), whose color darkened considerably on the addition of 18-crown-6 (0.49 g; 1.86×103 mole). The flask was stoppered, protected from light, and stirred for 28 hours at room temperature. The mixture was then poured into water (120 ml) and extracted with dichloromethane (4×50 ml). The combined organic extracts were dried (MgSO4) and evaporated to give viscous yellow oil (932.7 g). This oil was distilled from a small amount of CuCl to give a product showing some impurities on TLC. The oil was then chromatographed on silica gel, initially eluting with dichloromethane/petrol (1:1) to remove the impurities. The product was then eluted off the column with ethyl acetate/petrol (1:1). Evaporation of the solvent gave a colourless oil, which was distilled to give the desired styrylbutyl alcohol as a colourless oil b.pt. 150-152°/0.4 mbar. Yield 18.70 g; 69.2%.
Workup
- customThe initial reaction
Sources & evidence
- ORD record
- ord-55eaf0bbf5ec4e0aa02df751d6317658
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06225431B1
Reaction notes
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