Benzene, 1-(chloroMethyl)-3-(1-Methylethoxy)- synthesis
- Product Name:Benzene, 1-(chloroMethyl)-3-(1-Methylethoxy)-
- CAS Number:26066-16-0
- Molecular formula:C10H13ClO
- Molecular Weight:184.66
26066-15-9
26066-16-0
General procedure for the synthesis of 1-(chloromethyl)-3-isopropoxybenzene from [3-(propan-2-yloxy)phenyl]methanol: To a stirred solution of 3-isopropoxybenzyl alcohol (19.5 g, 116 mmol) in carbon tetrachloride (100 mL) was added triphenylphosphine (32 g, 122 mmol). The reaction mixture was heated to reflux for 12 hours. After completion of the reaction, the crude product was purified by silica gel column chromatography with 10% ethyl acetate/hexane as eluent, the target fraction was collected and concentrated under reduced pressure to give 1-(chloromethyl)-3-isopropoxybenzene (13.4 g, 64% yield) as a colorless liquid.
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Yield:26066-16-0 64%
Reaction Conditions:
with tetrachloromethane;triphenylphosphineReflux;
Steps:
To a stirred solution of the 3-isopropoxybenzylalcohol (19.5 g, 116 mmole) in carbontetrachloride was added triphenylphosphine(32 g, 122 mmoles) and the mixture was refluxed. The crude reaction was pre-loaded onto silica gel and chromatographed eluting with 10% EtOAc/hexanes to give the product (13.4 g,64%).
References:
Egbertson, Melissa;McGaughey, Georgia B.;Pitzenberger, Steven M.;Stauffer, Shaun R.;Coburn, Craig A.;Stachel, Shawn J.;Yang, Wenjin;Barrow, James C.;Neilson, Lou Anne;McWherter, Melody;Perlow, Debra;Fahr, Bruce;Munshi, Sanjeev;Allison, Timothy J.;Holloway, Katharine;Selnick, Harold G.;Yang, Zhiqiang;Swestock, John;Simon, Adam J.;Sankaranarayanan, Sethu;Colussi, Dennis;Tugusheva, Katherine;Lai, Ming-Tain;Pietrak, Beth;Haugabook, Shari;Jin, Lixia;Chen;Holahan, Marie;Stranieri-Michener, Maria;Cook, Jacquelynn J.;Vacca, Joseph;Graham, Samuel L. [Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,# 21,p. 4812 - 4819] Location in patent:supporting information
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